Synthesis, molecular structure, quantum chemical analysis, spectroscopic and molecular docking studies of N-(Morpholinomethyl) succinimide using DFT method

Article abstract of DOI:10.1016/j.molstruc.2018.07.101

N-(Morpholinomethyl) succinimide (SMF) bearing the empirical formula C₉H₁₄N₂O₃, has been synthesized by using the mannich condensation reaction. On considering its extensive pharmaceutical usage and medicinal value, we investigated its chemical structure and composition by employing various spectral techniques like ¹H, ¹³C NMR, UV-Visible spectroscopy, FT-IR, FT-Raman and TG/DSC techniques. Density Functional Theory (DFT) computation was adopted to study the electronic structure of the SMF molecule. Incorporating the VEDA 4 package, Total Energy Distribution (TED) was computed for vibrational assignment. In order to find out the strength and stability of the molecules an analysis based on the Natural Bond Orbital (NBO) was carried out. Gauge-Independent Atomic orbital (GIAO) was employed to confirm whether the ¹H and ¹³C NMR spectrum could show the chemical shift values. Frontier molecular orbitals in order to investigate the forbidden energy gap, viz., HOMO-LUMO were calculated and the λ_max values were observed. Frontier molecular orbitals were mainly identified which contributed the atomic orbitals. Based on the chemical activity, mapping of the figure was carried out on molecular electrostatic potential. The nature of molecular interaction was ascertained for molecular docking studies in which the biological protein system was reported. Based on the results, a suitable mechanism, its protein binding mode and drug action were presented. Molecular docking results suggested that the SMF molecule might exhibit inhibitory activity against the lung cancer protein.

Full text of DOI:10.1016/j.molstruc.2018.07.101

Accepted Manuscript
Synthesis, molecular structure, quantum chemical analysis, spectroscopic and
molecular docking studies of N-(Morpholinomethyl) succinimide using DFT method
K. Sarojinidevi, P. Subramani, Mani Jeeva, N. Sundaraganesan, Maria
SusaiBoobalan, G. VenkatesaPrabhu
PII:
S0022-2860(18)30926-8
10.1016/j.molstruc.2018.07.101
MOLSTR 25506
DOI:
Reference:
To appear in: Journal of Molecular Structure
Received Date: 5 May 2018
Revised Date: 18 July 2018
Accepted Date: 28 July 2018
Please cite this article as: K. Sarojinidevi, P. Subramani, M. Jeeva, N. Sundaraganesan, M.
SusaiBoobalan, G. VenkatesaPrabhu, Synthesis, molecular structure, quantum chemical analysis,
spectroscopic and molecular docking studies of N-(Morpholinomethyl) succinimide using DFT method,
Journal of Molecular Structure (2018), doi: 10.1016/j.molstruc.2018.07.101.
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Sign (λ2)ρ

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Synthesis, Molecular structure, Quantum chemical analysis, Spectroscopic
and Molecular docking studies of N-(Morpholinomethyl) succinimide using
DFT method
K.Sarojinidevia,P. Subramania*, Mani Jeevab, N. Sundaraganesanc, Maria SusaiBoobaland
G. VenkatesaPrabhue
aDepartment of Chemistry (Engg.), Annamalai University, Annamalai Nagar, 608 002
Chidambaram, Tamil Nadu, India.
bDepartment of Chemistry, National Institute of Technology, Tiruchirappalli-620015,
Tamilnadu, India.
cDepartment of Physics (Engg.), Annamalai University, Annamalai Nagar, 608 002
Chidambaram, Tamil Nadu, India.
dDepartment of Chemistry College of Natural and Computational Sciences
(CNCS),Haramaya University, Harar, Dire Dawa, Ethiopia.
eDepartment of Chemistry, National Institute of Technology, Tiruchirappalli - 620015,
Tamilnadu, India.
ABSTRACT
N-(Morpholinomethyl) succinimide (SMF) bearing the empirical formula
C9H14N2O3, has been synthesized by using the mannich condensation reaction. On
considering its extensive pharmaceutical usage and medicinal value, we investigated its
1
chemical structure and composition by employing various spectral techniques like H, 13C
NMR, UV-Visible spectroscopy, FT-IR, FT-Raman and TG/DSC techniques. Density
Functional Theory (DFT) computation was adopted to study the electronic structure of the
SMF molecule. Incorporating the VEDA 4 package, Total Energy Distribution (TED) was
computed for vibrational assignment. In order to find out the strength and stability of the
molecules an analysis based on the Natural Bond Orbital (NBO) was carried out. Gauge-
1
Independent Atomic orbital (GIAO) was employed to confirm whether the H and 13C NMR
spectrum could show the chemical shift values. Frontier molecular orbitals in order to
investigate the forbidden energy gap, viz., HOMO-LUMO were calculated and the λmax
values were observed. Frontier molecular orbitals were mainly identified which contributed
the atomic orbitals. Based on the chemical activity, mapping of the figure was carried out on
molecular electrostatic potential. The nature of molecular interaction was ascertained for

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molecular docking studies in which the biological protein system was reported. Based on the
results, a suitable mechanism, its protein binding mode and drug action were presented.
Molecular docking results suggested that the SMF molecule might exhibit inhibitory activity
against the lung cancer protein.
Keywords; Charge analysis; DFT; Moleculardocking; N-(Morpholinomethyl) succinimide;
Vibrational spectra; TED.
Corresponding author
1. Introduction
N-(Morpholinomethyl) succinimide(SMF), having the empirical formula C9H14N2O3,
it has been synthesized by using the condensation of aldehyde, imide and secondary amine.
The familiar morpholines molecules naturally or synthetically have a significant application
of pharmacological and biological with a great range structure core of organic molecules [1].
It is reported that the morpholine is widely used as an important building block in the field of
medicinal chemistry [2-4]. A new series of morpholine derivatives has been reported by
Micheli et al. [5] as a selective DAD3 receptor antagonist along with the data related to in-
vitro profile and pharmacokinetic. The presence of various nitrogen heterocyclic molecule in
morpholine derivatives play an important role as they occur in nature and biologically active
molecules, which carry the anti-inflammatory and antagonist properties and are used in some
chemical transformations as chiral auxiliaries [6]. Apart from having pharmacological
properties, the morpholines have their important application in a limited level as a simple
bases catalyst such as N-alkylating agent, catalysts and chiral auxiliaries in many organic
synthesized [7-13]. Pyrizinamide (morphozinamide), one of the derivatives of
morpholinomethyl is found to have more potential treatment properties with cure of
tuberculosis than the traditional pyrizinamide [14]. Several succinimide derivatives have
significant biological activities such as antiepileptic and anticonvulsive, fungicidal and other
pharmacological [15-19] activities. Nowadays, Mannich base compounds, in chemistry,

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express many opportunities for resourceful molecular system of biologically active and it is
dependent on the expectations and their needs. The Mannich base molecular structures
provide interaction of transition metal ions, which is the most valuable region in the
coordination chemistry. Varity of Mannich bases and their metal complex structures have
their individual creativity of biological importance and they play an important role in various
industrial applications. Bundgaard and co-workers have reported the application of N-
Mannich bases structure containing amine for antibiotics prodrug forms [20]. For illustration,
the salicylamide and aromatic amines with succinimide are presented in N-Mannich bases
compounds, which are used to identify the prodrug of therapeutic significance. Many
Mannich bases are offered with amazing biological activity. 1-[Anilino (phenyl) methyl]
pyrrolidine-2,5-dione is a group of Mannich base and its transition metal complexes have a
valuable microbial significance. The Mannich base molecular system of 1-[(pyridin-2-yl
amino) methyl] pyrrolidine-2,5-dione have their own biological activity expressly
performance on antioxidant property. The SMF is a white-crystalline powder which has a
₀
melting point in the range of 101 - 103 C. The compound SMF based on coarse aqueous
suspension, has acidity level of PH 6.2- 6.5. The studies of the SMF, both experimental and
biological have been conducted, but the vigorous literature survey reveals that there are no
theoretical investigations made on SMF molecule mainly focusing on the part of molecular
structure, spectral assignments, orbital, PDOS, electrostatic potential, thermodynamic
properties and molecular docking. The current work is dedicated to get the theoretical and
computational conclusion of the electronic structure, equilibrium molecular geometry,
vibrational modes (IR and Raman), NMR chemical shifts, mass spectral analysis and
TG/DSC techniques of the SMF molecule.

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2.Experimental Details
2.1. Synthesis of 1-(morpholinomethyl)Succinimide (SMF)
N-(Morpholinomethyl)Succinimide (SMF) was synthesized by Mannich condensation
reaction [21 - 23] among succinimide, morpholine and formaldehyde in 1:1:1 molar ratio.
Succinimide (5.00g, 0.05M) and morpholine (4.5 ml, 0.05M) mixed with the less amount of
ethanol was stirred until the content becomes homogenous. To this mixture 40 %
formaldehyde solution (3.8ml, 0.05M) was poured slowly in drops, as the stirring action
continued. Once the adding process was over, stirring continued for 2 h at 60°C and then it
was made to cool in refrigerator. The solid mass obtained was rinsed using distilled water,
desiccated and the final residue was recrystallized from acetonitrile to yield a colourless
crystalline powder (Yield: 88 %).
Reaction Scheme: 1
2.2. Experimental Method
The SMF molecule was synthesized and reported earlier [21- 23] and the Fourier
Transform Infrared spectrum of SMF was recorded on a Perkin Elmer FT-IR
spectrophotometer utilizing the KBr pellet (by mixing about 1–2 mg of the analyte with 300
- 400 mg of finely powdered KBr) strategy as a part of the range 4000 - 450 cm-1as shown in
Fig.1. Fourier Transform Raman spectrum was recorded on a BRUKER RFS 27 spectrometer
utilizing 1064 nm excitation wavelength from a Nd:YAG Laser in the district 4000 -50 cm-1
1
as appeared in Fig.2. The laser yield for this solid specimen is about 100 mW. H NMR
spectra of SMF molecule were recorded on Bruker500 MHz Advance NMR spectrometer
using TMS as an internal standard and its processing resonance frequency with the applied
radio-wave frequency at 0 ppm in δ-scale (the chemical shift value) as presented in Fig.3(a).
Furthermore, the sampling of the compound was done using highly polar protic solvent,
dimethyl sulfoxide (DMSO). Proton decoupled 13C NMR spectra were recorded on Advance
NMR Bruker spectrometer 500 MHz, with an operating frequency of about 75 MHz, by
using the deuterated dimethyl sulfoxide (DMSO) as a solvent as shown in Fig.3(b). TMS
was used as an internal standard. The HRMS analysis was done using High Resolution Q-

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TofMass, mass spectrometer as detector (Perkin Elmer), TurboMassver 5.4.2 software for
data analysis. The GC parameters were found as split 10:1 injection; column: Elite-5MS
(30m x 0.25 mm I.D, 250ꢀm df); injection port temperature: 250 °C; carrier gas: helium; flow
rate: 1 mL/min; oven temperature: initially 60 °C for 2 min, ramped to 300 °C at 10 °C/min,
300 °C for 6 min. The MS conditions found were as follows: transfer line heater: 240 °C; ion
source temperature: 240 °C; electron impact ionization (EI) mode; ionization energy: 70 eV.
Analysis was performed in scan mode, from 600 -10 amu at a speed of 1.5 scans/s. Solvent
delay was set as 2.0 min as observed in Fig.4 (a). The obtained mass spectra were compared
with commonly used EI-MS spectra libraries (NIST, Wiley 2008). TG/DSC study was
engaged with the thermo gravimetric instrument TGA7 (Perkin Elmer) Q500 Hi-Res TGA
from TA instruments), DSC7 (Perkin Elmer) Q200 Hi-Res TGA from TA instruments as
shown in Fig.4 (b). UV-Vis spectrum was recorded in DMSO solvent by employing the
Lambda-35 Perkin Elmer spectrophotometer as a part of the spectral locale of 1100-190 nm
as shown in Fig.S1 (Supplementary information).The entire spectrum experiment was
condensed at Indian Institute of Technology (IIT), Madras, India.
3. Computational Details
Density Functional Theory (DFT) calculations were employed in the Gaussian-09
program [24] package used in our study. The Becke three parameter hybrids functional
method has been employed in the work. It consists of non-local exchange functional of
Becke style three parameter sets and the non-local correlation functional of Lee, Yang and
Parr [25, 26]. The triple-split valence Gaussian function usually along with polarization
functional, for both bulky atoms and simple atom like hydrogen, 6-31G (d, p) basis sets have
been involved in the calculations. The saddle- point or stationary points as the energy due to
minima at the DFT level using harmonic vibrational analyses have been determined. The
vibrational spectrum bands were performed on account of the corresponding total energy
distribution (TED) calculated with the help of VEDA 4 program [27] while the GuassView
program [28] was employed to give a visual presentation of the vibrational assignments.
Natural Bond Orbital (NBO) analysis was adopted using NBO 3.1 program [29] incorporated
in Gaussian09W at B3LYP/6-31G (d,p) level, to find the inter- molecular delocalization
between the filled orbital and unfilled orbital and also to calculate the hyper conjugation. The
gauge independent atomic orbitals (GIAO) method [30, 31] along with the B3LYP/6-31G
1
(d,p) functional method was used to calculate the chemical shifts of the SMF molecule. H
and 13C isotropic magnetic shielding (IMS) of every X atom (carbon or hydrogen) was

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applied corresponding to the standard value of TMS, CSX = IMSTMS – IMSx. UV-Vis
spectra and electronic properties of molecular orbital energies were simulated by Time-
Dependent DFT (TD-DFT). The Density of states (DOS) was performed with the help of
Gauss- sum 3.0 software program [32].
3.1. Prediction of Raman Intensities;
The theoretical Raman intensity (IiR) is simulated by calculating Raman spectrum which can
be predicted using the formula [33] [34].
(IiR) =C(ν0 - νi)4 νi-1Bi-1Si
------------------------------------------------
(1)
Where the Bi is the temperature factor, which accounting for the intensity contribution of
excited vibrational states and its denoted by the Boltzmann appropriation (Bi)
-(hνi /KT)
Bi =1-exp
--------------------------------------------------- (2)
In this study, the IR equation, νi is the frequency of laser excitation line and we have utilized
i
the excitation frequency ν0= 9398.5 cm-1, which corresponds to the wavelength of 1064 nm
of a Nd:YAG laser. The νi represents the frequency of normal mode (cm-1), while the Si is the
Raman scattering activity of the normal mode Qi. The IR is assumed in arbitrary unit. In the
i
above said equation, the h and k denote Planck and Boltzmann constants, C and T represent
the speed of light and temperature in Kelvin, respectively.
4. Results and discussion
4.1. Molecular geometry
The complete geometrical optimization was accomplished by accepting the C1 point
group symmetry. The optimized molecular constitution of the most stable structure of SMF
molecule as B3LYP/6-31G (d, p) basic set is shown in Fig.5. By using B3LYP/6-31G (d, p)
method the structural parameters like bond lengths, bond angles and dihedral angles of the
titled molecule have been computed and optimized. The X-ray crystal data of the titled
molecule [21] are compared with the results obtained and presented in Table1. All the bond
lengths and bond angle values show small deviation when compared to the calculated XRD
values obtained by using the B3LYP/6-31G (d, p) basis set. The experimental values show
the molecule as solid state, whereas the theoretical calculation has predicted an isolated
molecule in gaseous state. The SMF molecule consists of electronegativity nitrogen atoms
bonded with the carbon (C8) atom of morpholine moiety. The carbonyl group (C═O) along
with the succinimide moiety by other termination acts as an electron acceptor. The charge
transfer involves over the π-conjugation among the electron contributor and acceptor groups.

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This SMF molecule contains fourteen C-H bonds, five C-C bonds, two C═O bonds, six C-N
bonds and two C-O bonds. The five membered rings consist of two dione at C1=O2, C5=O6
and lie in the range, obtained for DFT calculation 1.215 Å, 1.214 Å which are associated with
experimental data 1.201 Å and1.211 Å available from the literature [22]. The C10-O9 and
C14-O9 bond length calculated by B3LYP/6-31G (d, p) method are of the same value of
1.425 Å which is slightly deviated from the experimental data of a related molecule by
1.423Å and 1.409Å [21] respectively. The calculated C-N bond length in the morpholine ring
are C8-N12=1.444 Å, C11-N12 = 1.467 Å, C13-N12= 1.468 Å and in the succinimide ring
are C1-N7 = 1.392 Å, C5-N7 =1.393 Å, C8-N7 = 1.473 Å by B3LYP/6-31G (d, p). These
values are similar to the related experimental values such as 1.430, 1.449, 1.4535, 1.387,
1.375 and1.482 Å. The C-N bonds reveal impartial double bond properties in this fragment
which are compared to the normal value of the single C-N bond (1.47 Å) and C=N bond 1.22
Å assemble given in the literature [23]. The morpholine is elongated due to the presence of
C-C bond length exactly at the location of nitrogen and oxygen substitutions, which gives
bond lengths C10-C11 and C13-C14 leading to 1.531 Å and similarly in the succinimide
C1-C3and C4-C5 lead to 1.527Å and C3-C4 lead to 1.537 Å while the observed values are
1.497, 1.495, 1.498 and 1.494, 1.510 Å. The calculated C–C bond length in succinimide ring
varies from 1.527-1.537Å by the B3LYP/ 6-31G (d, p) which synchronize with recorded data
(1.494-1.510Å). The C- C bond lengths of the morpholine ring record the value as 1.531 Å.
The corresponding values are very near to experimental XRD values (1.495-1.497 Å). The
bond length C3-C4 has the maximum value (C3-C4=1.537 Å by B3LYP/ 6-31G (d, p), 1.510
Å by XRD) compared to the other C-C bond lengths. The electron deficient (carbonyl) group
present in the succinimide ring, due to the symmetry of the cyclic system is not disturbed.
The bond length C1-C3 =1.527 Å and C4-C5 =1.527Å is shorter than the C3- C4 =1.537Å
which is measured using DFT method at the other substitution. The maximum contraction in
the succinimide ring angle C3-C4-C5 is computed at 105.1° and the experimental result
shows good correlation with this value at 105.2°. The C-H bond length of the succinimide
and morpholine ring varies from 1.092 Å -1.105 Å which is found slightly greater than the
experimental value 0.970 Å. Whereas, small increment occurs in morpholine ring, the C-H
bond lengths C10-H21=1.095Å, C10-H22=1.105Å, C11-H23=1.098Å, C11- H24=1.094Å,
C13-H25 =1.098 Å, C13-H26 =1.094 Å, C14-H27 = 1.105 Å, C14-H28=1.095 Å have equal
values for C10-H22 and C10-H21of B3LYP/ 6-31G (d, p).

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4.2. Mulliken population analysis
Mulliken charge distribution of the SMF molecule was analyzed using the B3LYP/6-31G
(d, p) method. In order to assigned its compositional molecules such as N-methyl morpholine
and N-methyl succinimide. The results are summarized in Table S1 (Supplementary
information). The horizontal bar diagram of comparative Mulliken charge distributions is
displayed in Fig.S2 (Supplementary information). The comparison of Mulliken charge
distribution with the intact SMF molecule and its separated N-methyl morpholine indicate the
Mulliken population analysis as almost similar in the cyclic system and all the carbon atoms
and oxygen atoms show negative charge in both the SMF molecule and the N-methyl
morpholine moiety; whereas the atoms C8 exhibit some deviation between the SMF molecule
and the N-methyl morpholine. This confirms the impact of the attachment of the N-methyl
succinimide ring in the SMF molecule. Similarly, the N-methyl succinimide ring in the SMF
molecule displayed deviation of Mulliken charges from that of the separated N-methyl
succinimide moiety in the atom C8 space only. The atomic charge of C8 in the SMF
molecule shows positive compared with that of the separated N-methyl succinimide moiety.
Carbon atoms C1, C2 (having carbonyl group), C8 (attached with nitrogen atoms) C10, C14
(attached with oxygen atoms) are positive while other carbon atoms are negative and among
these, C1 and C5 are most positive which occurs due to the presence of a carbonyl group.
From the SMF molecule, the carbon atoms are nearly equally negative, but C11 and C13
found to be highly negative charged which naturally occur with specific movement of
electrons from N12 to carbon (morpholine ring). Atoms C10 and C14 in the SMF molecule
were computed with the less positive charge due to the presence of the oxygen atom. By
sharing the electron with neighbouring carbon atoms the hydrogen atoms found in SMF
molecule show positive results. The Mulliken atomic charges of the succinimide group
hydrogen atom H16 and H18 are higher than the morpholine group and the methylene group
hydrogen. It denotes the succinimide group hydrogen atoms as found more acidic than the
morpholine group and methylene group hydrogen atoms. However, the high value of 0.15038
and 0.15039 for H16 and H18 respectively with the B3LYP/6-31G (d, p) basis set. Mulliken
charge distribution analysis found the carbonyl, oxygen and nitrogen groups in the SMF
molecule as contributing factors positively to its biological activity.

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4.3. Dipole moment of SMF
The dipole moment of SMF molecule has the value of 2.0423 D representing the
vector components of the dipole moment along with Cartesian coordinates are summarized in
Table S2 (Supplementary information). The dipole moment value, on the whole is found far
greater when compared to water, [(H2O) µ =1.85 D]. The dipole moment of morpholine [µ
=1.71 D] is found lesser than that of title molecule while succinimide [µ =2.22 D] which is
greater than that of title molecule [35, 36]. Being a highly polar in nature, the SMF molecule
is found to be soluble, easily in polar solvents (methanol, ethanol, n-propanol, isopropanol, n-
butanol, acetone, DMSO, DMF and CHCl3) and this activity is found absent in the case of
certain polar organic compounds such as water, ether and partially soluble in CCl4, benzene
and acetonitrile [22]. The direction of dipole moment vector co-ordinates of SMF is shown in
Fig.S3 (Supplementary information). The electric dipole moment components data along with
cartesian coordinates, are considered as the magnitude of the total dipole moment is
preferably pointed towards the negative Z-direction, mainly consider as the electron
withdrawing group such as oxygen atoms placed at morpholine ring, carbonyl group at C1
and C5 and the Nitrogen atom found in N-CH2-N are all present in the positive X and Z-
direction. The remaining atoms are slightly often circulated among the additional two
Cartesian axes. The above inferences indicate an unsymmetrical charge separately distributed
within the molecule, but only partially extent around the molecule.
4.4. Vibrational analysis
The title SMF molecule has C1 symmetry and consisting of 28 atoms with 78 normal
modes of vibration, which may be distributed as 53 in-plane and 25 out-of-plane bending
vibrations. It is concluded that the FT-IR and FT-Raman are active on the vibrational modes.
The comparison of computed FT-Raman and FT-IR bands with experimental wavenumbers
and vibrational assignments are summarized in Table 2 and the theoretically constructed FT-
IR and Raman spectrum are shown in Fig.S4 (Supplementary information). The computed
wavenumber are scaled by 0.967 which was recommended by A.P.Scott [37].
4.4.1. C=O vibrations
In the case of five membered cyclic systems [38], the carbonyl group frequencies are
shown in the assortment 1830-1800 cm-1 and 1790-1740 cm-1. The experimentally reported
values of our studied molecule reflect strong and very strong band at 1765cm-1and 1737 cm−1
respectively in the FT-IR spectrum and very strong peak at 1769 cm−1 in the FT-Raman
spectrum, which are assigned as C=O stretching vibration. In the current studies, we have
noticed theoretically predicted strong, intense C=O stretching vibration corresponding to a

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wavenumber of 1800, 1740 cm-1. The TED for these vibrations, show 86 and 87%
contribution suggests that the above values are pure stretching vibrations. The observed value
of C=O group vibration is slightly lower than the theoretically calculated frequency and it is
indicated that the conjugation of the carbonyl(C=O) bond in the succinimide ring, increase
the single bond character, which gives a minimum value for carbonyl group stretching
wavenumbers [39]. In the FT-IR spectrum, the weakest band was observed at 934 cm-1 which
synchronizes to the theoretical wavenumber at 961 cm-1 and is related to the C= O stretching
vibration mode which is mixed with C-N and C-C stretching mode. In the SMF system, the
C=O in-plane and out-of plane bending vibrations are observed at 536 and 557 cm-1 in FT-IR
as the weak and very weak bands respectively. Similarly, the vibrations at 532 and 561cm-1
in FT-Raman as the weak and strong band respectively correlate well with the calculated
counterpart at 540 and 557 cm-1 with a TED contribution of 64 and 42% respectively. It is
coupled with C-C stretching and bending of CNC, in- plane of CCCH vibration mode. The
main attribute vibration of cyclic ether in the sequence from 1150–1085 cm−1 corresponds to
the C-O-C asymmetric stretching [40, 41]. The computed C-O-C asymmetric stretching
vibrations are observed at 1103 cm−1 and found to have perfect concurrence with the
experimental FT-IR value of 1110 cm−1.
4.4.2.C-N vibration
The identity of the C-N vibrations occurring in molecules, are generated to be complex and
allows several bands to get mixed in the following region. The C-N stretching vibration is
found 783 cm-1 in FT-Raman spectrum and in FT-IR the peak shows at 781 cm-1 which are
correlated well with the computed value at 780 cm-1 by B3LYP/6-31G (d, p) method with 58
% of TED impact. In addition to these vibrations, the C–N–C, N–C–N and C–C–N bending
vibrations (i.e. in plane and out-of-plane) have been designed by TED, showing good
concurrence with recorded observed data. The C-N in-plane bending harmonic vibrations
computed at 1359, 1338, 1194, 620, 470, 468, 254 cm-1 by B3LYP/6-31G (d, p) method show
excellent agreement with the FT-IR band at 621 cm-1 and FT-Raman bands at 608, 216 cm-1
are assigned to C-N in-plane bending vibrations. In the SMF molecule, the C-N torsion and
out-of plane bending vibrations are observed at 1245, 883, 557 and 428 cm-1 in FT-IR and at
1308, 884, 561 and 413 cm-1 in FT-Raman which correlate well with the theoretical
counterpart at 1319, 1235, 893, 557 and 430 cm-1 with a TED contribution of ~ 40%.

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4.4.3. CH2 vibration
The CH2-stretching region of morpholine is remarkably similar to that of piperazine,
except the changes in comparative intensities. The oxygen atom having a lone pair plays an
analogous role as that of nitrogen in changing the confident CH2 bands [42]. The intense
observed peak presented in the range such as 2800 -3000 cm-1 are considered with
overlapping due to the absorption peaks of stretching vibration of the CH2 group [43]. The
asymmetric CH2 stretching vibration usually observed in the range 3000 -2900 cm-1 while the
CH2 symmetric stretch appears to be 2900 and 2800 cm-1 [44, 45]. The bands at 2861 in FT-
Raman and 2880, 2867 cm-1 in the FT-IR is assigned to CH2 symmetric stretching vibrations.
The medium and strong intensity band at 3014, 2986, 2958 and 2944 cm-1 in FT-Raman and a
strong to very weak bands at 2986, 2961, 2938 and 2939 cm-1 in FT-IR are assigned to CH2
asymmetric vibrations of SMF molecule. The CH2 symmetric and asymmetric stretching
wavenumber of theoretical anharmonic frequencies by B3LYP method show best affiliation
with the recorded spectral data. The further related bands of CH2 group are tabulated in Table
2. The computed frequency of twisting and rocking of the CH2 vibrations, show a perfect
concurrence with the experimental observation values by B3LYP/ 6-31G (d, p).
4.4.4. C-C vibrations
For our SMF molecule, the C-C stretching vibration was predicted theoretically to appear
in the lower frequency range such as 1012 and 853 cm-1. The C-C stretching was observed at
985and 858 cm-1 as a strong band in FT-IR and in FT-Raman observed at 984 and 854 cm-1
which coincides with the theoretical counterpart value at 856 cm-1. The very strong peak was
obtained at 632 cm -1 in the FT- IR and observed at 661 cm-1 as a very strong, intense band in
FT-Raman correlate well with the theoretical wavenumber at 651cm-1 which occur due to the
presence of CCC in-plane bending vibration. The CCCC out of plane bending vibration is
computed at 84cm-1 theoretically which correlates well with FT-Raman at 76 cm-1 as a very
strong band with a TED vibration mode of 86 %.
4.5. NBO analysis
The Natural Bond Orbitals (NBO) calculations were predicted with NBO 3.1 program
[29] as appliance in the Gaussian 09 package by using B3LYP/6-31G (d, p) basis set and the
imperative results are summarized in Tables S3 and S4 (Supporting information). The
molecular system has an intramolecular hyperconjugative interactions such as C1-O2 from
N7 of n1(N7) → π*(C1-O2) where the electron density increases at 0.23363e weakening the
related bonds C1-O2 which evidently exhibit strong delocalized designate with the
stabilization of 54.47 kJ/mol; C5-O6 from N7 of n1(N7) → π*(C5-O6) and the electron

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density increases in the range at 0.22975e weakening the related bonds C5-O6 amount to a
stabilization of 53.57 kJ/mol; C5-N7 from n2(O6) → σ*(C5-N7) which increases the
electron density 0.09310e and weakens the respective bonds C5-N7 leading to stabilization of
28.78 kJ/mol; C1-N7 from n2(O2) → σ*(C1-N7) increases the electron density 0.06774e and
weakens the respected bonds C1-N7 which is related to stabilization energy of 28.48 KJ/mol;
C4-C5 from n2(O6) → σ*(C4-C5) gives electron density at 0.0679e and the respective bonds
weaken C4-C5, its lead to stabilization of 21.90 kJ/mol; C1-C3 from n2(O2) → σ*(C1-C3)
shows the electron density as increasing at 0.06774e and weakens the particular bonds N7-C8
which have a stabilizing energy of 21.86 kJ/mol; N7-C8 from n1(N12) → σ*( N7-C8) which
increases the electron density of 0.06540e and weakens the respective bonds C1-N7an
account of stabilization of 10.79 kJ/mol. The natural hybrid orbital with higher energies,
considerable p-characters are very close to almost (100%) and low occupation numbers such
as n2 (O9), n1 (N7), π(C5-O6) and π(C1-O2). The energies, p-characters, occupation
numbers of these orbitals are -0.27836, 0.26279,-0.37996 and -0.38072 a.u. and 99.88, 99.86,
99.83, 99.68, 99.82, 99.67 % and 1.86714, 1.58932, 1.98974 and 1.98968 a.u. The orbital
with lower energies and high occupation numbers are n1 (O2), n1 (O9), (C5-O6) and (C5-
N7). The energies, p-characters and occupation numbers of these orbital are -0.68199, -
0.55564, -1.09022, -0.81121a.u. and 42.55, 55.14, 66.21, 57.02,69.71 and 66.70% and
1.97553, 1.96729, 1.99606 and 1.98581a.u. Thus, a very close to pure p-type lone pair orbital
involve in the electron contribution to the σ*(C10-C11) orbital for n2(O9) → σ* (C10-C11) ,
π*(C1-O2) orbital for n1(N7) → π*(C1-O2), π*(C5-O6) orbital for n1(N7) → π*(C5-O6),
π*(C5-O6) orbital for C5-O6→ π*(C5-O6) and π*(C1-O2) orbital for C1-O2→ π* (C1-O2).
4.6. NMR Spectral analysis
The chemical shift analysis is the most significant technique adopted with design of
molecular geometry dimension essential for consistent calculations of magnetic properties,
1
after performing the full geometry of respected molecule. The H and 13C chemical shift
values in GIAO, related to TMS (act as a reference for title compound) were predicted by
using B3LYP/6-31G (d, p) level of theory; synchronize with the observed experimental
1
13
values. The experimental H and C NMR spectra of the SMF molecule in DMSO solvent
are presented in Fig.3 (a) and (b) respectively. The computed chemical shift values are in
conformity with the corresponding experimental data. The results are summarized in Table 3.
4.6.1.1H NMR spectrum of SMF

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The hydrogen atoms of the N-CH2-N group appear as singlet and the value was
observed at higher chemical shift of 4.21 ppm (DMSO) due to influence of nitrogen atom
1
with theoretical peaks at 4.68 ppm. The triplet at 3.52 ppm in the H NMR spectrum of this
compound shows the presence of methylene proton (N-(CH2)2) having the coupling constant
1
value of 4.75 Hz. The H NMR spectrum of SMF reveals a doublet at 2.44 ppm for four
protons attached to an oxygen group with the integral value corresponding to four protons
having the coupling constant of 4.5Hz. A multiplet peak was observed at 2.51 - 2.50 ppm
with four protons such as 15H, 16H, 17H and 18H (O=C-CH2). A multiplet was appeared in
the region of 2.51 - 2.50 ppm with four protons having the integral value which is always
assigned to the succinimide ring protons. The DMSO (solvent) peak was observed at 3.3 ppm
as shown in Fig.3 (a).
4.6.2.13CNMR spectrum of SMF
13
In C NMR spectrum, the progress of electrons from the oxygen atom having lone
pair to non-bonding σ orbital due to the existence of carbon atom in the carbonyl group has
low lying excited state, which produces a paramagnetic current [46]. This n- σ* produces a
higher to a lower intensity, since the carbonyl carbon peaks occur due to the presence of
higher wavenumber and it can appear in the range from 150-220 ppm [47, 48]. Thus, it has
helped to identify the chemical shift value of a carbonyl group from the rest of the
resonances, for the SMF molecule the carbonyl group has absorption at 179.13 ppm, which
was compared with calculated value of 159.32 ppm in gas phase and 163.26 ppm in solvent
(DMSO). In 13C NMR spectrum of SMF, the absorption of seven aliphatic carbons give
signals in the region 28.64 to 66.51 ppm, the peak at 28.64 ppm is due to the carbon(C4)
attached to the carbonyl carbon which was compared with the computed value at 23.69 ppm
in the gas phase and 20.55 ppm in DMSO solution. The electronegative atom of oxygen,
attached to carbon C10 and C14 shows a higher wavenumber, thus the NMR signal was
observed in the downfield at 66.51 and 59.69 ppm and the NMR signal was calculated at
59.80 and 58.84 ppm in gas phase and in solvent phase at 54.56 & 53.71ppm. The electron
withdrawing atom present in the adjacent position, gives the chemical shifts in the de-
shielded region. The signals at 40.48 and 40.31 ppm are related to the carbon C11 and C13
respectively show a deviation of theoretical value at 48.27 and 46.73 in gas phase and 43.32
and 41.91ppm in solvent (DMSO) phase. The highest electronegative property present in the
nitrogen (N) atom gives the electron contribution around the bond to polarise through the
neighbouring carbon atom; the electron density was found decreased at the association for the

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SMF molecule. Therefore, the results seem to have slightly higher value for the SMF
molecule under study at 50.90 ppm (C8) as predicted with the theoretical value at 52.81 in the
gas phase and 48.99 in solvent (DMSO) phase. The DMSO (solvent) peak was observed at
40.24 - 39.48 ppm as shown in Fig.3 (b).
4.7. Mass spectrum of SMF
Mass Spectrum of SMF analysis was done with the HRMS method. In general, the
calculated mass was appeared at m/z 198.22 (high predominant) and 199.1083(less
predominant). Similarly, in the experiment interestingly matching with less predominant, the
base peak, at m/z 199.11, it is related to the most stability of the Molecular ion peak
+
[C9H14N2O3 ] of our compound. It shows a peak at m/z 200.11 corresponding to [M+H]
+peak and as represented by protonated of molecular ion, on account of the fragment of
+
C9H15N2O3 . The 13C, 15N, and 33S mainly contribute to the M+1 peak, of which the 13C is the
most significant. If the M is range up to 100%, hence the M+1 intensity/1.1% which gives an
approximation for the quantity of carbon atom present in the molecule. The peak observed at
+
m/z 209.09, due to the fragment [C4H6N2O2 ], indicates an isotope peak of carbon atoms. The
peak appears at m/z 221.08, is related to the molecular ion with sodium metal ion
[C9H14N2NaO3]+. The two peaks observed at m/z170.10 and 181.11 have values
corresponding due to the fragment of C8H14N2O2 and C9H18N2O2.The disintegration pattern
proposes as a molecular mass of SMF as 199.11 and nitrogen rule is also related by this
corresponding value. The mass spectrum of SMF molecule is shown in Fig. 4(a).
4.8. TGA and DSC studies of SMF
The simultaneous TGA and DSC method was used to find the thermal stability and
decomposition behaviour of the SMF molecule. The TGA and DSC study found the heating
at the rate of 10 ºC/min from surrounding temperature to 600ºC/min in nitrogen atmosphere
as shown in Fig.4 (b) [49]. From the TGA curve it is clear that until the melting point (102ºC)
is reached, there is absence of weight loss, since the material is represented as the unreality of
crystallization solvent or contamination and the most definite thermal stability of SMF up to
beginning of melting point. The flat response of TGA plot after its melting point indicates the
thermal decomposition of SMF with the formation of reaction products [50]. It takes place in
two stages, the first mass loss occurs at 270.6 ºC - 300 ºC and suffers 88.41% mass fraction
loss, due to the liberation of volatile substances like morpholine ring. The next mass loss
takes place at 320 to 600.3 ºC on the description of the volatile product like N-Succinimide
and residue left about 96.34% found towards the end. The final residual carbon mass at 600.3

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ºC represents the end of the composition reaction is 3.40%. The second broad exothermic
peak appears at 275 ºC and after this stage the mass loss in TGA occurs gradually. The
gradual mass loss represents the liberation of succinimide fragments [51]. The decomposition
temperature found as 270.6 ºC in TGA graph, above its melting point, represents the thermal
stability of the SMF molecule. The significant weight loss below 270.6ºC indicates the title
SMF molecule as devoid of physically adsorbed water and water of crystallisation. The final
residual carbon mass at 600.3 ºC indicates the last part of the composition reaction is 3.40%.
From the graph, it is obvious that the sharp exothermic peak with an onset, peak maximum
with offset appear at 100, 114.0 and120ºC. The exothermic peak related to the activity of the
sample melting point liberating the facilitating the process of melting. The second board
exothermic peak was shown at 270.6 ºC. The maximum peak value and height of the peak
will be indicated by sample weight and possibly by encapsulation procedure, hence the poor
thermal conduct produces lower peak height with broader peak [52, 53]. It is determined by
the purity of the sample and to analyze the curve obtained by a DSC plot with its shape. The
higher concentration of an impurity in a given sample lower the melting point and broader the
range. In SMF molecule, the highest melting point and the sharpness of the DSC melting
peak reveal that SMF has higher crystallinity and purity.
4.9. UV-Visible spectral analysis
The recorded UV-Vis spectrum of SMF molecule is shown in Fig. S1 (Supplementary
Information) and computed absorbance, oscillator strength and transition assignment are
shown in Table 4. This spectrum shows that absorbance maxima for SMF molecule is at 287
nm due to possibility of n- π * transition which involve the transfer of electron from non-
bonded atomic orbitals along with carbonyl O-atom to the first molecular excited state of
SMF. The frontier molecular orbital analysis considers the HOMO as comparatively having
large orbital co-efficient due to N-atom with one set of the lone pair of electrons residing on
its sp3 hybridized orbitals. Consequently, the non-bonded orbital of the O-atom having lone
pairs are equally responsible for the assorted approaches of electronic excitation in the
absorbance of SMF. Furthermore, the UV-Vis spectrum of SMF is shown in Fig.S5
(supplementary information) has been simulated by the TD-DFT model. The calculated
observed spectrum gives a broader peak; which is slightly deviated from the observed
experimental results λmax value of SMF. The computed UV-Visible absorbance maximum
appeared at 275 nm. The discrepancy with the experimental and computed values might be
due to the short sightedness of the chosen DFT model and expected tolerance limit of 12 nm.

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The experimental results mainly depend on factors such as solvent, concentration, solvation
effect and molecular interactions.
4.10. Frontier molecular orbital analysis
The HOMO-LUMO energy gap plays an important role in determining the chemical
reactivity, chemical reactions and strength of the molecule, UV-Vis spectra, electrical and
optical properties. The HOMO-LUMO band gap was analysed through conjugated molecule,
which provides an important role of specific movement of electron take place through the end
capping nucleophilic groups like electron-donor atom to the effective electrophilic groups
like electron-acceptor atoms with pi-conjugated bridge. The strong electronic interaction
through pi-conjugated path results in considerable ground state donor-acceptor assimilation
the appearance of an electron transfer band in the electronic spectrum. Therefore, electron
transport properties localized over the morpholine group of the pi-conjugated molecule in the
electron-donor (HOMO) side of its electron withdrawing part (LUMO). The electrical
transport properties of molecules, for investigating the most reactive position that take place
in pi-conjugated systems and also gives a numerous number of reactions in the conjugated
system were explained by using an energy band gap between HOMO and LUMO has been
done. In SMF molecule, there are 53 valence electrons presented in molecular orbitals, which
is the highest occupied molecular orbital (HOMO) having unsymmetrical properties (A)
among the energy of about -5.56 and also for lowest unoccupied molecular orbital (LUMO)
having energy with -0.30 eV. It consists of 280 molecular orbitals and the atomic orbitals,
mostly distributions towards the HOMO and LUMO, can be visualized from Fig. 6(a) and the
obtained data are summarized in Table 5. Evidently, the HOMO and the LUMO of SMF
molecule are primarily having a linear mixer of atomic orbitals of nitrogen on morpholine
ring and the two adjacent carbonyl atoms at positions 2 and 5 of succinimide ring. The band
gap or excitation energy between the frontier molecular orbitals is determined as ∆E (LUMO-
HOMO) and found to be -5.26 eV. The electronic transition of the λmax computed wavelength
by B3LYP/6-31G (d, p) method has been contributed of H→L (99%) followed by H-1→L
(95%) and H→L+1 (98%) for the solvent (DMSO) phase. The Gauss Sum 3.0 software [32]
is used to predict the group contribution of the molecular orbit (DOS) for the SMF molecule
in the gas and solvent phase as shown in Fig.6 (a). The PDOS spectrum represents bonding
and anti-bonding interaction, due to positive overlap population and negative overlap
population analysis [54] are shown in Fig.6 (b). The HOMO orbital is found on the
morpholine ring, methylene group of succinimide ring, CH2 and C=O bond are represented as

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(84%+9%+25%+3%+1%) and the LUMO corresponds to the succinimide ring, C=O and
methylene group of succinimide ring with the contribution of (60%+30%+6%).
4.11 Reduced Density Gradient (RDG) analysis
The real space weak interaction, based on electron density and derivatives is
approached by RDG analysis and it is developed by Johnson et al. [55]. It is a dimensionless
quantity and the first gradient found in the literature.
∆
2ρ(r)
1
RDG = (r) =
-------------------------- (3)
1
3
4
3
2
2(3
π
r )
ρ(r)
The weak interaction is identified by analyzing by low electron density values. The plot of
RDG vs ρ provides the presence of interaction strength. The λ2 sign is used to differentiate the
bond (λ2<0) interactions from non-bonding (λ2 > 0) interaction. The Multiwfn and VMD
software [56, 57] are used to plot the RDG surface for the SMF molecule. The RDG = 0.1 in
the molecular denote the molecule having repulsive shown in the Fig.7 and attractive
interaction. The value near to zero on both sides denote the equal possibility of attraction and
repulsion in the molecular system. The gradient isosurface are mention in colour by the
values of (λ2) ρ, which represent the interaction strength in the molecular system seen from
colour ranging from blue to red (stronger attraction to repulsion). As we look refer Fig.7, the
red colour represents the ring system which is responsible for steric effect, the green colour
represents the van der Walls (VDW) interaction which denote that the electron in the region
are low.
4.12. Thermodynamic simulation properties of SMF
According to the principles of statistical thermodynamics and the standard
thermodynamic function such as heat capacities at constant volume (CV), entropies (S), and
enthalpy changes (E) for the SMF molecule were computed from the theoretical harmonic
frequencies predicted from B3LYP/6-31G (d, p) basic set in the temperature range of 100 -
1000 K are given in the Table S5 (Supplementary Information). It can be evaluated that the
all values in thermodynamic functions are found increasing with the temperature which varies
from 100 to 1000 K due to the increase in molecular vibrations intensities with increase in
temperature. From the computed data, the quadratic fitting equations have been derived along
with their factors (R2). By using these equations (4, 5, 6), we can predict the attributes at any
point of temperature without further computational procedures. It is inferred from the results

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that the thermodynamic parameters linearly depend on the temperature value. The
correlations between the thermodynamic properties and temperatures T values are shown in
Fig.S6 (Supplementary Information). The correlation equations are as follows:
E= -0.025+0.187T-7х10-5T2 (R2=0.998)
CV =146.8+0.016T+6х10-5T2 (R2=0.999)
S =61.41+0.193-4х10-5T2 (R2=1)
------------------------------------------ (4)
------------------------------------------- (5)
------------------------------------------- (6)
They can be used to predict the thermodynamic energy function based on the theory of
relationship with thermodynamic variables and used to evaluate the directions of chemical
behaviour following the thermodynamics second law in the thermochemical field [58].
4.13. Molecular Electrostatic Potential (MEP)
Molecular electrostatic potential (MEP) designed with the space about the
molecule due to species distribution, is very useful in interpreting and predicting reactive
charges of electrophilic and nucleophilic reaction for the investigation of biological
identification and intermolecular hydrogen bonding interaction. The electrostatic potential
provides information to analyze the processes according to the identification in the region of
the molecule, as in drug-receptor and enzyme-substrate interactions, since this is through
possibilities that the both species primary distinguish from each other. The MEP plot display
the most probable reactive path of the respected molecule for an interaction with electrophilic
and nucleophilic charges, MEP of SMF molecule at the DFT/B3LYP method with 6-31G (d,
p) basic set optimized geometry was calculated. Negative region generally represented as red
colour which is due to the presence of electrophilic reactivity of the represented molecule,
whereas the blue colour indicates nucleophilic reactivities which are related to the presence
of positive electrostatic potential of respected molecules as shown in Fig.S7 (supplementary
information). The electronegative atoms having lone pair are usually associated with the
negative electrostatic potential region. From the MEP plot of the SMF molecule, the negative
region of the electrostatic potential is in C=O groups of succinimide ring and the oxygen
atom of morpholine ring which are electrophilic. The maximum electrostatic potential arises
due to the positive region as well in the region due to the presence of the nitrogen atom and
hydrogen atoms which are nucleophlic. The result of MEP provides that clear evidence for
the biological activity of the SMF molecule
.
4.14. Molecular docking studies

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Molecular docking study is one of the recent virtual simulation techniques used to find
the binding site of protein-ligand site. The PASS (Prediction of Activity Spectra) [59] online
tool is used for prediction of protein for ligand interaction. In our study, the PASS online
result is shown in Table S6 (Supplementary Information). For molecular docking, the high
resolution fine crystal structure of tumour suppressor in lung cancer 1 (PDB ID: 2HE7) [60]
is used. We utilized Auto Dock 4 software package. Initially the protein was kept ready with
the help of Auto Dock tools graphical [61] user interface. The polar hydrogen atoms were
added to the protein, atomic charges were calculated by kollman method and lamarckian
genetic algorithm (LGA) was utilized for molecular docking calculation implemented in Auto
dock 4.0 software package [62]. The ligand PDB molecule was created by using the
optimized molecular geometry. The active site to the energies was defined to add the residues
of active site with the use of grid size 80Ǻ×80Ǻ×80Ǻ using Autogrid [63, 64].
With the
help of Auto Dock software [62] the binding energy (Kcal/mol), inhibition constants (µM),
intermolecular energy (Kcal/mol) were computed in Table S7 (Supplementary Information),
The best result i.e lowest binding result is shown in 2HE7 protein exhibit the lowest binding
energy (-4.14 Kcal/mol) with inhibition constant value of 927.56 (µM) as shown in Table S8
(Supplementary Information). In Fig.8, the yellow dotted line implies the formation of
hydrogen bonds of ligand with target proteins, hydrogen bond involved in the protein - ligand
is illustrated using pymol software [65]. The analysis shows the point that lung cancer amino
acid of LYS187, ASP149, LYS148, LEU153 form H-bond with C=O and O of title ligand
with hydrogen bond length of 2.0, 2.9, 3.4 and 2.4 Ǻ shows the existence of the ligand-
protein interaction as shown in Table S8(Supplementary Information). The obtained finding
from the PASS online and our computed result molecule might have potential inhibitor
against the lung cancer protein.
5. Conclusion
The derivative of novel mannich base SMF molecule was synthesized and it has been
characterized using vibrational, NMR, UV- Vis, mass and TG/DSc techniques. The DFT
computations were used to predict the structural geometry and vibrational frequencies. The
FT-IR recorded spectrum was investigated with the aid of Density Functional obtained from
both experimental and theoretical studies confirming the presence of CO, C-O-C, and N-CH2-
N functional group. In the UV, the λmax values of the SMF molecule were nearly similar in
the liquid and gas phases, indicating the implications of optical activity of the molecule in the
solvent as negligible. The DFT calculation with higher basis set predicted the Raman shifts as

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especially a good deal compared to the experimental data. The HOMO was restricted over the
morpholine ring except the succiniminide ring, whereas the LUMO was presented over the
succinimide ring which resulted in the electron transfer process in molecular orbital. The
MEP plot of the SMF molecule and negative region was mainly around over the C=O groups
of succinimide ring and the oxygen atom of morpholine ring which were represented as
electrophilic. The highest positive region was presented on the Nitrogen atom and hydrogen
atoms which indicated as nucleophlic. The molecular docking study concludes with the fact
that the SMF molecular has might inhibitor activity against protein, which indicates against
the lung cancer as evident from the binding energy of-4.14 Kcal/mol. This result identifies
the inhibitory activity against lung cancer disease.
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ACCEPTED MANUSCRIPT
Table 1
Geometrical parameters [bond length (Å), bond angle ( ͦ ) and dihedral angle ( ͦ)] of the SMF molecule.
Bond
length
B3LYP/61
3-G (d, p)
XRDa
Bond angle
B3LYP/613
-G (d, p)
127.4
124.7
107.8
105.2
108.7
108.7
113.5
113.7
107
XRDa
Dihedral angle
B3LYP/61
3-G (d, p)
-178.3
59.8
-56.3
2
-119.9
124.0
178.0
2.4
XRDa
176.2
O2-C1-C3
O2-C1-N7
C3-C1-N7
127.3
124.3
108.4
105.1
111.0
111.0
111.0
111.0
109.0
105.2
111.0
111.0
111.0
109.0
126.6
109
124.4
112.2
122.9
123.6
116.7
108.0
108.0
108.0
108.0
107.0
110.21
111.5
111.2
109.0
109.0
110.0
110.0
108.0
109.8
109.0
109.0
110.0
110.0
108.0
114.7
115.2
110.7
109.5
110.0
110.0
110.0
110.0
108.0
111.5
109.0
109.0
109.0
109.0
108.0
O2-C1-C3-C4
C2-C1-C3-H15
C2-C1-C3-H16
N7-C1-C3-C4
N7-C1-C3-H15
N7-C1-C3-H16
O2-C1-C3-C5
O2-C1-N7-C8
C3-C1-N7-C5
C3-C1-N7-C8
C1-C3-C4-C5
C1-C3-C4-H17
C1-C3-C4-H18
H15-C3-C4-C5
H15-C3-C4-H17
H15-C3-C4-H18
H16-C3-C4-C5
H16-C3-C4-H17
H16-C3-C4-H18
C3-C4-C5-O6
C1-O2
C1-C3
C1-N7
1.215
1.527
1.392
1.537
1.094
1.093
1.527
1.094
1.094
1.214
1.393
1.473
1.444
1.094
1.092
1.425
1.425
1.531
1.095
1.105
1.467
1.098
1.094
1.468
1.531
1.098
1.094
1.105
1.095
1.201
1.498
1.387
1.510
0.970
0.970
1.494
0.970
0.970
1.211
1.375
1.482
1.430
0.970
0.970
1.423
1.409
1.497
0.970
0.970
1.449
0.970
0.970
1.454
1.495
0.970
0.970
0.970
0.970
C1-C3-C4
−4.5
C3-C4
C1-C3-H15
C1-C3-H16
C4-C3-H15
C4-C3-H16
H15-C3-H16
C3-C4-C5
C3-C4-H17
C3-C4-H18
C5-C4-H17
C5-C4-H18
H17-C4-H18
C4-C5-O6
C3-H15
C3H-16
C4-C5
C4-H17
C4-H18
C5-O6
−176.9
−9.5
3.7
171.1
3.6
-2.3
-177.9
-1.1
105.1
113.7
113.4
108.9
108.5
107
127.6
107.8
124.6
114
C5-N7
N7-C8
-120.1
117.4
117.6
-1.4
-123.9
-119.8
121.2
-1.4
-179.8
-0.2
-57.6
122.0
58.5
C8-N12
C8-H19
C8-H20
O9-C10
O9-C14
C10-C11
C10- H21
C10-H22
C11-N12
C11-H23
C11-H24
N12-C13
C13-C14
C13-H25
C13-H26
C14-H27
C14-H28
C4-C5-N7
O6-C5-N7
C1-N7-C5
C1-N7-C8
123.2
122.6
112.3
105.6
105.6
112.6
111.3
109.1
111.7
110.8
106.4
110
111.3
110.1
108.1
111.9
108.5
111.5
108.0
109.2
107.6
116.6
116.1
111.4
111.7
108.2
109.1
108.6
111.3
107.8
110.9
109.9
106.4
110.2
111.3
108.0
178.6
−1.6
C5-N7-C8
C3-C4-C5-N7
N7-C8-N12
N7-C8-H19
N7- C8-H20
N12-C8-H19
N12-C8-H20
H19-C8-H20
C10-O9-C14
O9-C10-C11
O9-C10-H21
O9-C10-H22
C11-C10-H21
C11-C10-H22
H21-C10-H22
C10-C11-N12
C10-C11-H23
C10-C11-H24
N12-C11-H23
N12-C11-H24
H23-C11-H24
C8-N12-C11
C8-N12-C13
C11-N12-C13
N12-C13-C14
N12-C13-H25
N12-C13-H26
C14-C13-H25
C14-C13-H26
H25-C13-H26
O9-C14-C13
O9-C14-H27
O9-C14-H28
C13-C14-H27
C13-C14-H28
H27-C14-H28
H17-C4-C5-O6
H17-C4-C5-N7
H18-C4-C5-O6
H18-C4-C5-N7
C4-C5-N7-C1
C4-C5-N7-C8
O6-C5-N7-C1
O6-C5-N7-C8
-121.9
1.5
177.2
-178.8
-3.2
−1.31
−168.6
178.5
11.2
C1-N7-C8-N12
C1-N7-C8-H19
C1-N7-C8-H20
C5-N7-C8-N12
C5-N7-C8-H19
C5-N7-C8-H20
N7-C8-N12-C11
N7-C8-N12-C13
H19-C8-N12-C11
H19-C8-N12-C13
H20-C8-N12-C11
H20-C8-N12-C13
C14-O9-C10-C11
C14-O9-C10-H21
C14-O9-C10-H22
C10-O9-C14-C13
C10-O9-C14-H27
C10-O9-C14-H28
O9-C10-C11-N12
O9-C10-C11-H23
O9-C10-C11-H24
H21-C10-C11-N12
H21-C10-C11-H23
H21-C10-C11-H24
H22-C10-C11-12
H22-C10-C11-H23
H22-C10-C1H24
88.5
101.5
-34.6
-150.1
-86.8
150.2
34.7
118.7
-106.9
-122.3
12.1
0.5
135
-58.5
-179.7
63.5
−92.6
−62.2
68.0
58.5
−58.9
−57.2
58.6
-63.5
179.8
54.6
-64.5
177.2
172.8
53.7
-64.6
-67.3
173.6
55.3

ACCEPTED MANUSCRIPT
C10-C11-N12-C8
C10-C11-N12-C13
H23-C11-N12-C8
H23-C11-N12-C13
H24-C11-N12-C8
H24-C11-N12-C13
C8-N12-C13-C14
C8-N12-C13-H25
C8-N12-C13-H26
C11-N12-C13-C14
C11-N12-C13-H26
N12-C13-C14-O9
N12-C13-C14-H27
N12-C13-C14-H28
H25-C13-C14-O9
H25-C13-C14-H27
H25-C13-C14-H28
H26-C13-C14-O9
H26-C13-C14-H27
H26-C13-C14-H28
85.3
-51.2
-155.3
68.3
-38.6
-175.1
-85.6
154.9
37.9
−171.5
56.2
171.7
57.7
51.1
174.6
-54.7
67.3
-172.9
64.5
-173.5
-53.7
-176.9
-54.9
64.8
aTable from Ref[21 -23]

ACCEPTED MANUSCRIPT
Table 2. Vibrational wavenumbers obtained for SMF at B3LYP /6-31G(d, p) method [harmonic frequency (cm−1), IR int(Kmmol-1),
Raman Intensity (Arb Units)].
Theoretical
Wavenumber (cm-1)
Experimental
Mode
nos.
TED (≥10%)
Assignments
Wavenumber(cm-1)
B3LYP
scaled
FT-IR
FT-Raman
IR int
RamInt
νCH(99)
νCH(98)
νCH(99)
νCH(97)
νCH(96)
νCH(95)
νCH(95)
νCH(99)
νCH(99)
νCH(98)
νCH(93)
νCH(84)
νCH(96)
νCH(94)
3452 br
1
2
3031
3030
3018
3011
3004
2992
2990
2988
2982
2970
2940
2935
2870
2862
6.06
4.29
0.04
11.1
13.88
45.47
55.1
2.71
12.9
11.5
62.89
13.4
81.13
26.3
49.86
13.13
26.4
26.22
22.2
99.71
68.95
110.46
25.08
29.03
60.66
10.15
77.08
8.22
3
4
3014s
5
6
7
8
2986ms
2986ms
9
10
11
12
13
14
15
16
17
18
2961ms
2938vw
2939w
2880ms
2867s
2958vs
2944vs
2861s
2810ms
2833w
2747vw
2697vw
2763w
2706vw
2651vw
19
20
21
22
23
24
25
26
27
28
2546vw
2269vw
2168vw
2080vw
1966w
1765s
νOC(86)
νOC(87)
1769vs
1800
1740
30.51
583.44
34.32
0.15
1737vs

29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
1714vs
ACCEPTED MANUSCRIPT
βHCH(62)
1463
1458
1449
1443
1442
1424
1422
1396
1381
1369
1359
1345
1338
1320
1319
1280
1274
1271
1235
1228
1205
1194
1139
1133
1124
1103
1066
1061
1033
1013
1011
993
5.13
3.81
35.62
10.32
31.56
44.55
49.28
20.3
βHCH(61)
βHCH(89)
0.09
5.07
5.9
30.72
0.3
55.92
1.48
5.87
βHCH(87)
βHCH(73)
1441vw
1428vw
βHCH(58)
1434s
βHCH(90)
52.58
7.22
19.81
8.62
τHCNC(49) + βCNC(10)
τHCOC(38) + γCHCH(28)
τHCNC(54)
1393s
1387ms
1362vw
1391w
βHCN(34)+ τHCNC(13)
γHCCH(14) + βHCN(12)
βHCN(56)
1.86
42.96
6.49
34.67
306.42
6.63
28.31
89.56
33.64
1.33
11.23
4.9
39.49
13.11
9.32
50.88
0.58
7.16
11.97
4.65
31.07
28.25
20.94
8.53
1349vs
1324vs
τHCOC(17) + γCHCH(16) + τHCNC(13)
τHCNC(26)+ βCNC(10)
βHCO(71)
1321ms
1308s
βHCC(23)+ τHCCC(19)
τHCNC(15)
1274vs
1245s
1228w
1203s
βHCC(36)+ τHCCC(19)+τHCCN(16) + νCC(13)
βHCO(30)+ τHCOC(11)
βHCC(30)+ γCCCH(23)+τHCCC(11)
βHCO(37)+βHCN(26)
νNC(14) + τHCNC(12) + γCCOH(10)
νNC(32)
1224vw
1210vw
1196w
1140s
0.43
37.68
61.66
48.58
1.91
66.76
72.85
31.26
17.78
2.08
1148vs
1133s
1121s
1110vs
1072s
1059s
1039s
βHCC(35)+τHCCC(19)+ τHCCN(12) + γCCCH(11)
νOC(75)
9.58
3.07
15.54
1.69
1.34
νCN(22)+ γCCOH(10)
γCCOH(21) + νNC(10)
νCC(21)+ βHCN(13)
νCC(36)+νCN(36)
1070w
1028s
7.24
βCCO(16) + νNC(11)+ βCCN(10)
γCCCH(56)+ γOCNC(22)
νCC(69)
1014vw
1000w
985ms
934w
883s
855vw
1014s
999s
984s
37.32
0.04
3.42
46.11
7.58
20.15
14.74
0.19
18.58
6.88
14.06
36.27
4.16
0.14
33.89
44.3
10.58
1.09
40.93
11.54
29.36
72.22
98.54
11.2
979
961
893
853
829
824
809
780
νOC(33)+νCC(37) + νNC(10)
τHCNC(11)
884s
854s
νCC(46)
νOC(53)+ νCC(11)
νNC(21)+ γCCOH(16)
γCCCH(31)+ γOCNC(24)
νNC(58)+ βNCN(11)
νCC(36) + βNCN(15) + νNC(13)
βCCC(74)
821ms
826
781vw
732w
632vs
783ms
739vs
661vs
719
651