Novel dibenzosuberene substituted aroyl selenoureas: Synthesis, crystal structure, DFT, molecular docking and biological studies

Article abstract of DOI:10.1080/10426507.2019.1699924

A series of aroyl selenourea dibenzosuberene (1–3) derivatives were synthesized and characterized by different analytical methods and single crystal X-ray crystallography. Quantum chemical computations were made using DFT to determine the structural and molecular properties of the compounds. The in?vitro antibacterial action of the compounds was evaluated against chosen gram-negative (Pseudomonas aeruginosa, Klebsiella pneumoniae, and Escherichia coli), and gram-positive (Bacillus subtilis, Staphylococcus aureus, and Staphylococcus epidermidis) bacteria for their antifungal activity against Curvularia lunata, Penicillium notatum, and Aspergillus niger. Using molecular docking studies, the binding modes were understood along with the mechanism in opposing the target protein MurB.

Full text of DOI:10.1080/10426507.2019.1699924

Phosphorus, Sulfur, and Silicon and the Related Elements
ISSN: 1042-6507 (Print) 1563-5325 (Online) Journal homepage: https://www.tandfonline.com/loi/gpss20
Novel dibenzosuberene substituted aroyl
selenoureas: Synthesis, crystal structure, DFT,
molecular docking and biological studies
Moideen Musthafa, Ramaiah Konakanchi, Rakesh Ganguly & Anandaram
Sreekanth
To cite this article: Moideen Musthafa, Ramaiah Konakanchi, Rakesh Ganguly & Anandaram
Sreekanth (2019): Novel dibenzosuberene substituted aroyl selenoureas: Synthesis, crystal
structure, DFT, molecular docking and biological studies, Phosphorus, Sulfur, and Silicon and the
Related Elements, DOI: 10.1080/10426507.2019.1699924
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PHOSPHORUS, SULFUR, AND SILICON AND THE RELATED ELEMENTS
https://doi.org/10.1080/10426507.2019.1699924
Novel dibenzosuberene substituted aroyl selenoureas: Synthesis, crystal
structure, DFT, molecular docking and biological studies
Moideen Musthafaa, Ramaiah Konakanchib, Rakesh Gangulyc, and Anandaram Sreekantha
b
aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli, India; Chemistry Division, H&S Department, Vignan Institute of
c
Technology and Science, Deshmuki, Hyderabad, India; Division of Chemistry & Biological Chemistry, Nanyang Technological University,
Singapore, Singapore
ABSTRACT
ARTICLE HISTORY
Received 10 September 2019
Accepted 28 November 2019
A series of aroyl selenourea dibenzosuberene (1–3) derivatives were synthesized and characterized by
different analytical methods and single crystal X-ray crystallography. Quantum chemical computations
were made using DFT to determine the structural and molecular properties of the compounds. The
in vitro antibacterial action of the compounds was evaluated against chosen gram-negative
(Pseudomonas aeruginosa, Klebsiella pneumoniae, and Escherichia coli), and gram-positive (Bacillus sub-
tilis, Staphylococcus aureus, and Staphylococcus epidermidis) bacteria for their antifungal activity
against Curvularia lunata, Penicillium notatum, and Aspergillus niger. Using molecular docking studies,
the binding modes were understood along with the mechanism in opposing the target protein MurB.
KEYWORDS
Antibacterial; antifungal;
molecular docking; DFT;
single-crystal XRD
GRAPHICAL ABSTRACT
1. Introduction
chemopreventive, anti-inflammatory, and anti-virus proper-
ties.[4] Selenium’s antinuclear properties have been proven
in most animals and in vitro studies, mostly at nutritional
levels. Additionally, there is a possibility of not only selen-
ium front prevention but also cancer treatment.[5,6] Over the
past decade, novel agents have emerged as anticancer agents
of them, selenium, which has molecules, has shown a greater
interest in cancer prevention and protection.[7]
Selenium is known as a biological trace element for the
development and well-being of animals and humans.[1]
Health benefits have attracted the most attention to selen-
ium, as it is a cancer prevention agent.[2,3] Over the past
four decades, epidemiological studies have shown low mor-
tality rates in areas with high levels of selenium. Selenium is
known primarily for its antioxidant function and its healing,
CONTACT Anandaram Sreekanth
Ganguly rganguly@ntu.edu.sg
sreekanth@nitt.edu
Department of Chemistry, National Institute of Technology, Tiruchirappalli, 620015, India; Rakesh
Division of Chemistry & Biological Chemistry, Nanyang Technological University, Singapore, 639798, Singapore.
Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/gpss.
Supplemental data for this article is available online at https://doi.org/10.1080/10426507.2019.1699924.
ß 2019 Taylor & Francis Group, LLC

2
M. MUSTHAFA ET AL.
corresponding to amide N ꢁ H. Aroyl selenourea N ꢁ H
appeared at 3294–3311 cmꢁ1.C ¼ O stretch frequencies were
observed in 1657–1670 cmꢁ1. The characteristic absorption
of C ¼ Se vibrations appeared in the range of
1156–1167 cmꢁ1, which agrees with previously reported
compounds.[27] The FTIR spectra of the compounds (1–3)
are shown in Figure S3 (supplementary material).
1H NMR spectra of the compounds revealed that the
N ꢁ H proton between carbonyl and selenocarbonyl group
appeared as singlets around 9.04–9.15 ppm and peaks in the
range of 11.64–11.89 ppm were assigned to N ꢁ H proton
present between selenocarbonyl and suberenyl sp3 carbon.
Peaks in the region of 6.93–6.29 ppm were assigned to sub-
erenyl N ꢁ CH proton. The aromatic protons appeared as
multiplets in the region 6.15–7.78 ppm. Signals at
178.5–179.0 ppm (C ¼ Se) and at 156.9-166.4 ppm (C ¼ O)
respectively appeared in the 13C NMR spectrum. The aro-
matic carbons of aroyl selenourea were observed in the
range of 112.0–146.1 ppm. 77Se NMR spectra of the com-
pounds revealed C ¼ Se peaks in the region of
417.20–404.02.The spectra are shown in Figure S4 (1H
NMR, supplementary material), Figure S5 (13C NMR, sup-
plementary material), and Figure S6 (77Se NMR), Mass spec-
Scheme 1. Synthesis of aroyl selenourea compounds (1–3).
Organic derivatives that include selenium have other
medical applications, and are biologically active substances
with anti-viral, anti-bacterial, antihypertensive, and fungi-
cidal properties.[8] A variety of organoselenium compounds
(such as heterocycles, selenocarbamates, and selenoureas),
among them, selenourea derivatives are significant
candidates.[9–12]
Recently, selenoureas have emerged as free radical
scavengers, enzyme inhibitors, anticancer agents with
other biological aspects.[13–16] Thus selenoureas can be uti-
lized to develop new chemotherapeutic agents.[17–20]
Dibenzosuberene (5 H-dibenzo[a,d]cycloheptene) are bio-
logically active molecules. Generally, bulky compounds tra of the compounds (1–3) are shown in Figure S7
(supplementary material).
move through a sterile shelter to mobilize a movement and
increase the penetration of lung by lipophilicity.The steric
characteristics of dibenzosuberene resembles 5 H-dibenzo[b,-
f]azepine-5-carboxamide (Carbamazepine), and is used as an
anticonvulsant or antiepileptic drug.[21–24] The compounds
(1–3) were represented by utilizing different spectroscopic
2.3. Single-crystal XRD analysis
The molecular structures of compounds 1 and 2 were fur-
ther confirmed by single-crystal XRD studies. The crystal
systems. Computational investigations were performed using refinement parameters of (1-2) are given in Table S3 (sup-
DFT studies to get data of the fundamental properties of the plementary material). The structures of (1-2) with atomic
labeling and crystal packing are displayed in Figures 1–3.
Selected interatomic bond lengths and bond angles are pre-
sented in Tables 1 and 2. The compounds 1 and 2 crystalli-
ses into monoclinic and triclinic lattice, respectively, with
space groups P121/n1 and P-1. The crystal structures of 1
and 2 revealed a possible intramolecular hydrogen-bonding
interaction between the carbonyl group and N (2)–H.
Furthermore, the selenourea C ¼ Se bond lengths were com-
parable to earlier reported selenourea compounds indicating
less distortions in the molecular structure.[28]
compounds, from which we undertook FMO and MEP stud-
ies. The HOMO and LUMO energies were also evaluated to
demonstrate the chemical stability of the molecules. In vitro
antibacterial and antifungal activity studies of the new com-
pounds were investigated.
2. Results and discussion
2.1. Synthesis
The 5 H-dibenzo[a,d][7]annulen-5-amine was prepared
according to standard procedure (Figure S1, supplementary
material).[25] The new N-dibenzosuberene substituted aroyl
selenoureas (1–3) were prepared by adopting the reported
method (Scheme 1).[26]
2.4. DFT studies
2.4.1. MEP analysis
Molecular electrostatic potential (MEP) maps describe the
charge density of molecules three-dimensionally and predict
nucleophilic and electrophilic centers in them .[29–31] The
2.2. Characterizations
[32,33]
MEP V(r) at a point r is represented as
ꢀ
ð
The electronic spectra of the compounds (1–3) showed
absorption bands around 270–283 nm, and 314–324 nm cor-
VðrÞ ¼ RN ðZA=jr ꢁ RAjÞ ꢁ
q ðr’Þ d3r’=jr ꢁ r’j
A
ꢀ
ꢀ
responding to p ! p and n ! p , transitions (Table S1,
supplemental materials). The UV–visible spectra of the com-
pounds (1–3) are shown in Figure S2 (supplementary mater-
ial). The Fourier-transform-infrared spectra of the
compounds (1–3) (Table S2, supplementary material)
where N is the total number of nuclei in the molecules.
The molecular electrostatic potential of the compounds
(1–3) is shown in Figure S8 (supplementary material). The
graphic illustration with
a rainbow color scheme of
showed peaks in the range of 3370–3398 cmꢁ1 Molecular electrostatic potential (MEP) is within the range

PHOSPHORUS, SULFUR, AND SILICON AND THE RELATED ELEMENTS
3
Figure 1. Thermal ellipsoid plot with atomic labeling of 50% probability of 1.
Figure 2. Thermal ellipsoid plot with atomic labeling of 50% probability of 2.
of ꢁ6.138 eꢁ2 to þ6.138 eꢁ2, ꢁ6.315 eꢁ2 to þ6.315 eꢁ2
,
2.4.2. Frontier molecular orbital analysis
ꢁ6.018 eꢁ2 to þ6.108 eꢁ2 for (1–3), respectively. The nega-
tive potential shows high-electron density is indicated in
red in the figure. The low-electron density (positive poten-
tial) is indicated in blue. Aroyl selenoureas have high-elec-
tron density and are progressively susceptible to
electrophilic attack.
Frontier molecular orbitals (HOMO and LUMO) and their
energies are important parameters for spectroscopists in the
field of quantum chemistry. LUMO energy represents
the ability to accept an electron, HOMO energy is related to
the ability to donate an electron. The energy difference
between HOMO and LUMO characterizes their molecular

4
M. MUSTHAFA ET AL.
Table 2. Bond lengths (Å) and bond angles (ꢂ) selected for 2.
Bond lengths (Å)
C6-Se1
C5-N1
C7-N2
C1-S1
1.842(5)
1.378(7)
1.474(6)
1.695(6)
C5-O1
C6-N2
C6-N1
C4-S1
1.231(7)
1.332(7)
1.390(7)
1.714(6)
Bond angles (ꢂ)
C2-C1-S1
C3-C4-S1
C5-C4-S1
O1-C5-N1
O1-C5-C4
C6-N2-C7
112.1(4)
112.0(4)
117.2(4)
123.1(5)
120.7(5)
123.1(4)
N1-C5-C4
N2-C6-N1
N2-C7-C8
N2-C7-C21
C5-N1-C6
C1-S1-C4
116.1(5)
117.2(5)
111.6(4)
110.8(4)
126.2(4)
91.6(3)
Figure 3. Crystal packing of compounds (a) 1 and (b) 2.
small energy gap has more polarization property, low kinetic
stability and is in general called a soft molecule. These mole-
cules can be explained as the resistance toward the deform-
ation of electron cloud and polarization of chemical systems
during the chemical process. Chemical softness is a useful
concept the behavior of chemical systems and is related to
their stability and low reactivity. Chemical hardness is a use-
ful concept to predict the behavior of chemical systems and
is related to the stability of a chemical system. Global hard-
ness g and chemical potential m of the compounds are given
by using the relation g ¼ (–EHOMOþ ELUMO)/2 ¼ 1.76, 1.66,
and 1.76 eV, m ¼ (EHOMOþELUMO)/2 ¼ –3.36, ꢁ3.64, and
3.52 eV and the Electrophilicity index (x) ¼ m2/2g can be
interpreted as a measure of energy reduction due to max-
imal electron flow between the donor and acceptor.[40] Soft
molecules have small hardness, while the hard ones have
large chemical splitting compounds (1–3) Electrophilicity
index values are found to be 6.39, 7.98, and 7.04 eV, respect-
ively. The calculated values describe the catalytic and bio-
logical activity of the title compound. The atomic orbital
components of the frontier molecular orbital are shown in
Figure 4.
Table 1. Bond lengths (Å) and bond angles (ꢂ) selected for 1.
Bond lengths (Å)
Se1-C1
C1-N1
C1-N2
1.829(2)
1.379(3)
1.317(3)
C2-O1
C2-N1
C9-N2
1.226(3)
1.386(3)
1.474(3)
Bond angles (ꢂ)
O1-C2-N1
N1-C2-C3
N2-C1-Se1
N2-C9-C10
C1-N2-C9
122.2(2)
O1-C2-C3
N2-C1-N1
N1-C1-Se1
N2-C9-C23
C1-N1-C8
120.8(2)
115.8(2)
118.08(16)
107.19(18)
127.25(19)
117.02(19)
126.10(17)
112.21(18)
125.10(19)
chemical stability. Furthermore, the LUMO energy is dir-
ectly related to electron affinity.[34,35] This is used to esti-
mate frontier electron density predict the most reactive
position in p-electron systems. It is also used to explain sev-
eral types of reactions in conjugated systems.[36] Conjugated
molecules are characterized by a small separation between
HOMO and LUMO, which is the result of a significant
degree of intermolecular charge transfer from the end-
capping electron-donor groups to the efficient electron-
accepter groups through an p-conjugated path.[37] To under-
stand various aspects of pharmacological formulations
including drug design and the possible ecotoxicological
characteristics of drug molecules, several new chemical
reactivity descriptors have been proposed. Conceptual DFT-
based descriptors have helped in many ways to understand
the structure of molecules and their reactivity by calculating
the chemical potential, global hardness and electrophilicity.
Using, HOMO and LUMO orbital energies, the electron
affinity (A), ionization energy (I), chemical potential (m),
Global hardness (g), and global electrophilicity power (m) of
2.5. Molecular docking studies
MurB is a flavoprotein, also known as UDP-N-acetylenol-
pyruvoylglucosamine reductase. It catalyzes the decrease of
an enolpyruvyl uridine diphosphate-N-acetyl glucosamine,
which is the second step in the biosynthesis of a bacterial
cell’s peptidoglycan layer. The reduced product, UDP-N-ace-
tyl muraic acid, acts as a locus for peptide portion attach-
ment to the cell wall. These cross-links are responsible for
cell rigidity. So MurB is an important enzyme in bacterial
cell wall synthesis. We have chosen E. coli: MurB (PDB ID:
1MBB) as the target protein, which was recovered
(httpww.rcsb.org/pdb) from the Protein Data Bank.[41–43]
Among all compounds, compound 1 exhibited good
inhibition activity against the protein 1MBB is indicated by
its lower binding energy value ꢁ5.31 kcal/mol. The docking
results are shown in Table 3. The compound 3 forms three
hydrogen bonds and the residues involved in the interaction
with compounds are PROA111, PROA219, ARG219,
ASPA220, respectively as seen in the figure. Compound 3
[38]
a compound can be calculated as
A ¼ ꢁELUMO; I ¼ ꢁEHOMO; l
¼ ðEHOMO þ ELUMOÞ=2; g
¼ ðꢁEHOMO þ ELUMOÞ=2 and x ¼ l2=2g:
HOMO and LUMO energy values are calculated at
B3LYP/6-311þþG(d,p) basic set. Energy values of the com-
pounds (1–3) are, EHOMO ¼ –5.12, –5.31, and –5.29 eV and
ELUMO ¼ –1.59, –1.98, and –1.76 eV, respectively. Energy
gaps of HOMO and LUMO in the compounds (1–3) are
found to be 3.53, 3.33, and 3.53 eV, respectively. The results
are represented in Table S4 (supplementary material). also displayed excellent activity against 1MBB protein with
According to Parr et al.[39] As mentioned, the molecule with binding energy values ꢁ 5.63 kcal/mol. The docking poses of

PHOSPHORUS, SULFUR, AND SILICON AND THE RELATED ELEMENTS
5
Figure 4. LUMO and HOMO energy level of compounds (1–3).
Table 3. MurB (PDB ID: 1MBB) docking parameters of compounds (1–3).
No. of rotational
bonds
best binding
energy (kcal/mol)
Inhibition
constant (Ki) lM
Compound
1
Amino acid residues involved in an interaction with compounds
3
ꢁ5.31
74.35
Pi –Anion : GLU A323 (4.60 Å)
Pi-Alkyl : LYS A232 (4.61 Å)
Amide – Pi stacked : ASN (2.61 Å) A233 (2.27 Å).
Pi-Alkyl : PRO A221 (3.85Å), PRO A111 (4.63 Å)
Pi –Anion : GLU A48 (5.57Å),ASP A220 (3.27 Å).
Pi-Alkyl : LYS A222, PRO A221 (4.27 Å)
2
3
3
3
ꢁ4.18
ꢁ5.63
86.62
128.14
Hydrogen bond : PRO A111 (5.13 Å), PRO A219 (2.59 Å), ARG 219, ASP
A220 (3.23 Å).
Pi-sigma : LEU A218.
the compounds (1–3) with the protein 1MBB are shown in exhibited moderate activity with MIC values of 18.6 mg/mL
Figures S9–S11 (supplementary material).
and 25.6 mg/mL, correspondingly. Compound 3 showed
good activity against A. niger with MIC values of 19.4 mg/
mL and moderate activity against P. notatum and C. lunata
with MIC values of 11.4 and 24.8 mg/mL, respectively.
Compounds 1 and 2 showed medium to low antifungal
activity with MIC values of 25.3–63.2 lg/mL against the
test strains.
2.6. Antimicrobial activity
Compounds (1–3) were evaluated for their in vitro anti-
microbial action against both gram-negative (G-) and gram-
positive (Gþ) bacteria strains and different fungal
strains[44–47] using Streptomycin and Nystatin as reference
controls. The MIC is illustrated in Tables S5 and S6 (supple-
mental materials). The minimum inhibitory levels are indi-
cated. The information shows that in vitro antimicrobial
activity was considerable against almost all antibacterial and
antimicrobial strains.
3. Materials and methods
All reagents were purchased from Alfa-Aesar and Sigma-
Aldrich. All the solvents were dried and purified according
to standard procedures. Elemental analyses (C, H, N, and S)
Among tested compounds (1–3), compound 3 has a wide were performed on a Vario EL III Elemental analyzer instru-
range of activity with MIC values of 10.5 mg/mL (S. aureus), ment. UV–visible spectra were recorded in DMF solution
11.9 mg/mL (B. subtilis), 9.5 mg/mL (S. epidermidis), 3.6 mg/ using analytic Jena SPECORD S600 spectrophotometer. FT-
mL (E. coli), 10.8 (K. pneumoniae), and 21.8 (P. aeruginosa), IR spectra in a range 4000 ꢁ 400 cmꢁ1were recorded on a
respectively, compared to Streptomycin. Compound
1
Perkin Elmer FT-IR/FIR Frontier spectrometer. NMR spec-
against K. pneumoniae, and compound 2 against B. subtilis tra were recorded in CDCl3 or DMSO-d6 using TMS as an

6
M. MUSTHAFA ET AL.
internal standard on a Bruker 500 MHz spectrometer. 4.1.3. N-((5H-dibenzo[a,d][7]annulen-5-yl)carbamosele-
noyl)furan-2-carboxamide (3)
Melting points were determined in open capillary tubes on a
Lab India melting point apparatus.
Yield: 1.06 g, 76%. Pale yellow solid. m.p.: 140 ꢂC. Anal.
Calc. for C21H16N2O2Se (%): C, 69.98; H, 4.47; N, 7.77; S,
8.90. Found: C, 69.82; H, 4.73; N, 7.59; S, 8.98. UV–vis
(DMF): kmax, nm 287, 309. FT-IR: V, cmꢁ1 3402, 3294
4. Experimental section
1
(N ꢁ H), 3058 (¼C ꢁ H), 1657 (C ¼ O), 1265 (C ¼ Se). H
NMR (500 MHz, CDCl3): d, ppm 11.64 (s, 1H, NH), 9.15 (s,
1H, NH), 7.64 (d, J ¼ 7.3 Hz, 2H), 7.46 (s, 1H), 7.43 (d,
J ¼ 7.6 Hz, 2H), 7.41– 7.37 (m, 3 H), 7.33 (t, J ¼ 7.5 Hz, 3 H),
7.23 (d, J ¼ 3.0 Hz, 1H), 6.80 (s, 1H), 6.49 (d, J ¼ 1.9 Hz,
1H). 13C NMR (125 MHz, CDCl3): d, ppm 178.5 (C ¼ Se),
156.9 (C ¼ O), 146.1, 145.0, 136.5, 133.7, 131.0, 129.7, 128.8,
127.8, 118.3, 114.3, 113.1, 112.0. LC-MS ¼ 425.5 [M – H]–.
4.1. Synthesis of N-dibenzosuberene substituted
compounds (1–3)
Compounds (1–3) were prepared by the following method.
A solution of benzoyl chloride (0.6 mL, 5 mmol) or thio-
phene-2-carbonyl chloride (0.6 mL, 5 mmol) or furan -2-car-
bonyl chloride (0.5 mL, 5 mmol) in dry acetone (25 mL) was
added dropwise to potassium selenocyanate (0.4859 g,
5 mmol) in dry acetone (25 mL). The reaction mixture was
stirred for one hour at room temperature. After cooling,
dibenzosuberenyl amine (1 g, 5 mmol) dissolved in acetone
(30 mL) was added to it dropwise, and the resulting mixture
was refluxed for 2 h at 65 ꢂC. The reaction mixture was
mixed with into hydrochloric acid (0.1 N, 200 mL) and the
resulting pale yellow/brown substance was filtered off.
Recrystallisation purified the solid product from a chloro-
form/ethanol mixture (1/2).
5. Conclusion
Spectroscopic techniques including FTIR, UV–visible, 1H
and 13C NMR spectra were used to characterize and confirm
the structure of dibenzosuberene substituted aroyl sele-
nourea derivatives. The molecular structures were evaluated
using single-crystal X-ray diffraction. Compounds 1 and 2
belong to monoclinic (1) and triclinic (2) crystal systems,
with space groups P121/n1 and P-1, containing four and
two molecules per unit cell, respectively. In vitro antimicro-
bial activity results revealed that compound 3 exhibited
good antibacterial and antifungal activity against tested
microorganisms compared to standards like Streptomycin
and Nystatin. Docking results revealed that compound 3
had the least binding energy against receptor MurB with a
binding energy value of –5.63 kcal/mol. The results indicate
that in silico molecular docking studies correlated well with
the experimental antibacterial activity results.
4.1.1. N-((5H-dibenzo[a,d][7]annulen-5-yl)carbamosele-
noyl)benzamide (1)
Yield: 1.18 g, 78%. Yellow solid. m.p.: 164 ꢂC. Anal. Calc. for
C23H18N2OSe (%): C, 74.57; H, 4.90; N, 7.56. Found: C,
74.31; H, 5.01; N, 7.65. UV–vis (DMF): kmax, nm 285, 312.
FT-IR: V, cmꢁ1 3399, 3311 (N ꢁ H), 3055 (¼C ꢁ H), 1670
1
(C ¼ O), 1283 (C ¼ Se). H NMR (500 MHz, CDCl3): d, ppm
11.89 (s, 1H, NH), 9.04 (s, 1H, NH), 7.77–7.72 (m, 4 H),
7.61 - 7.58 (m, 2 H), 7.52 - 7.38 (m, 8 H), 7.28 (d,
J ¼ 13.1Hz, 1H), 6.88 (s, 1H). 13C NMR (125 MHz, CDCl3):
d, ppm 178.3 (C ¼ Se), 166.4 (C ¼ O), 136.5, 133.8, 133.4,
131.8, 131.0, 129.7, 129.0, 128.8, 127.8, 127.3. LC-MS ¼
419.3 [M – H]–.
Acknowledgements
The authors Moideen Musthafa and Ramaiah Konakanchi are grateful
to MHRD, Government of India, for giving
Research Fellowship.
a
Senior
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4.1.2. N-((5H-dibenzo[a,d][7]annulen-5-yl)carbamosele-
noyl)thiophene-2-carboxamide (2)
Yield: 1.20 g, 79%. Yellow solid. m.p.: 170 ꢂC. Anal. Calc. for
C21H16N2OSeS (%): C, 59.57; H, 3.81; N, 6.62; O, 3.78; S,
7.57. Found: C, 59.39; H, 3.29; N, 6.42; O, 3.78; S, 7.44.
UV–vis (DMF): kmax, nm 274, 321. FT-IR: V, cmꢁ1 3377,
3298 (N ꢁ H), 3058 (¼C ꢁ H), 1665 (C ¼ O), 1273 (C ¼ Se).
1H NMR (500 MHz, CDCl3): d, ppm 11.28 (s, 1H, NH), 8.77
(s, 1H, NH), 7.65 (d, J ¼ 7.2 Hz, 2H), 7.60 (d, J ¼ 4.7 Hz,
1H), 7.56 (d, J ¼ 2.9 Hz, 2H), 7.44 (d, J ¼ 7.6 Hz, 3H), 7.40
(td, J ¼ 7.5, 1.0 Hz, 3H), 7.34 (t, J ¼ 7.1Hz, 1H), 6.79 (s, 1H),
6.37 (d, J ¼ 2.0 Hz, 1H). 13C NMR (125 MHz, CDCl3): d,
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¼
407.8 [M–H]–.

PHOSPHORUS, SULFUR, AND SILICON AND THE RELATED ELEMENTS
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