Synthesis and characterization of N-(2,2-Diphenylacetyl)- N′-substituted thiourea derivatives: The crystal structure of N-(2,2-Diphenylacetyl)-N′-(4-chloro phenyl)-thiourea

Article abstract of DOI:10.1080/10426500902979743

A series of new N-(2,2-diphenylacetyl)-N′-substituted thiourea derivatives (1-9) have been prepared and characterized by elemental analyses, IR and 1H NMR spectroscopy. N-(2,2-diphenylacetyl)-N′-(4-chlorophenyl)- thiourea was also characterized by a singl

Full text of DOI:10.1080/10426500902979743

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Synthesis and Characterization
of N-(2,2-Diphenylacetyl)-
N′-Substituted Thiourea
Derivatives: The Crystal
Structure of N-(2,2-
Diphenylacetyl)-N′-(4-chloro
phenyl)-thiourea
Demet Sezgin Mansuroğlu a , Hakan Arslan a , Don
VanDerveer b & Gün Binzet c
a Department of Chemistry, Faculty of Pharmacy,
Mersin University, Mersin, Turkey
b Department of Chemistry, Clemson University,
Clemson, South Carolina, USA
c Department of Chemistry, Faculty of Arts and
Science, Mersin University, Mersin, Turkey
Published online: 18 Nov 2009.
To cite this article: Demet Sezgin Mansuroğlu , Hakan Arslan , Don VanDerveer &
Gün Binzet (2009): Synthesis and Characterization of N-(2,2-Diphenylacetyl)- N′-
Substituted Thiourea Derivatives: The Crystal Structure of N-(2,2-Diphenylacetyl)-N′-
(4-chloro phenyl)-thiourea, Phosphorus, Sulfur, and Silicon and the Related Elements,
184:12, 3221-3230
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Phosphorus, Sulfur, and Silicon, 184:3221–3230, 2009
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500902979743
Synthesis and Characterization of N-(2,2-Diphenylacetyl)-
Nꢀ-Substituted Thiourea Derivatives: The Crystal
Structure of N-(2,2-Diphenylacetyl)-Nꢀ-(4-chloro
phenyl)-thiourea
1
1
˘
Demet Sezgin Mansuroglu, Hakan Arslan,
2
3
¨
Don VanDerveer, and Gun Binzet
1Department of Chemistry, Faculty of Pharmacy, Mersin University,
Mersin, Turkey
2Department of Chemistry, Clemson University, Clemson, South
Carolina, USA
3Department of Chemistry, Faculty of Arts and Science, Mersin
University, Mersin, Turkey
A series of new N-(2,2-diphenylacetyl)-N ꢀ-substituted thiourea derivatives (1–9)
have been prepared and characterized by elemental analyses, IR and 1H NMR
spectroscopy. N-(2,2-diphenylacetyl)-N ꢀ-(4-chlorophenyl)-thiourea was also char-
acterized by a single crystal X-ray diffraction study. The compound crystallizes in
the monoclinic space group P21/c with Z = 4 and a = 9.6551(19) Å, b = 20.060(4)
Å, c = 9.894(2) Å, β = 104.29(3)◦. The molecular conformation of the compound is
stabilized by an intramolecular (N1-H1···O1) hydrogen bond that forms a pseudo-
six-membered ring.
Keywords Pseudo-six-membered ring; single crystal structure determination; synthe-
sis; thiourea
INTRODUCTION
Thiourea derivatives have attracted much attention due to their chemi-
cal properties and their biological activities.1 Some thiourea derivatives
have been found to be useful as insecticides, fungicides, herbicides,
and plant-growth regulators.2–4 In recent years, thiourea derivatives
have been the subject of special attention because it has been shown
that they have antitumor bioactivities, antifungal bioactivities, and
Received 3 March 2008; accepted 20 April 2009.
This work was supported by Mersin University Research Fund (Project No:
BAP.ECZ.F.TB.(HA).2007–1).
Address correspondence to Hakan Arslan, Department of Chemistry, Faculty of
Pharmacy, Mersin University, 33169, Mersin, Turkey. E-mail: arslanh@mersin.edu.tr;
hakan.arslan.acad@gmail.com
3221

˘
D. S. Mansuroglu et al.
3222
inhibitor activities against viruses.2,5–7 In addition, thiourea deriva-
tives have been widely applied in many research fields, such as the
separation of platinum group metals and the extraction of trace el-
ements.8–12 The thiourea derivatives have also received much atten-
tion because the existence of a thiocarbonyl group in these compounds
enhances their coordination ability. Particularly the presence of oxy-
gen, nitrogen, and sulfur donor atoms provides a variety of bonding
possibilities. These derivatives react with transition metals mostly in
monoanionic and bidendate form by deprotonation, resulting in neutral
complexes with sulfur and oxygen coordination.13
In the past few years, we have pursued investigations on the synthe-
sis, characterization, crystal structure, thermal behavior, vibrational
analysis, antifungal activity, and antibacterial activity of new thiourea
derivatives.14–33 Based upon a literature search, we found no data on
the synthesis or characterization of thiourea derivatives of the type
presented here.
In this article, we report the preparation and characterization of
nine new thiourea derivatives and the crystal and molecular structure
of N-(2,2-diphenylacetyl)-Nꢀ-(4-chlorophenyl)-thiourea.
RESULTS AND DISCUSSION
All thioureas 1–9 were prepared according to the method of Douglass
and Dains34 and were obtained in yields ranging from 85% to 94%
(Scheme 1). The synthesis involves the reaction of a 2,2-diphenylacetyl
chloride with potassium thiocyanate in acetone followed by conden-
sation of the resulting 2,2-diphenylacetyl isothiocyanate with an ap-
propriate primary amine. The compounds were purified by recrystal-
lization from ethanol:dichloromethane mixtures and characterized by
1
elemental analysis, H NMR, and IR spectroscopy. The analytical and
spectroscopic data are consistent with the proposed structures.34,35 The
synthesis of intermediate and target compounds 1–9 were performed
by the reactions illustrated in Scheme 1.
The main vibrational bands of the compounds 1–9 are given in the
experimental section. The characteristic νNH stretching vibrations of
N,N-dialkyl-Nꢀ-benzoylthiourea derivatives are expected to appear in
the 3450–3100 cm−1 frequency range.14–17,32–38 The room temperature
attenuated total reflection Fourier transform infrared spectra of the
new compounds show two bands at ∼3250 cm−1 and ∼3180 cm−1 due to
νNH stretching vibrations.36 This difference between the νNH stretching
vibration frequencies is due to intramolecular hydrogen bonding (X-ray

N-(2,2-Diphenylacetyl)-N ꢀ-Substituted Thiourea Derivatives
3223
SCHEME 1 Synthesis reaction of the compounds.
single crystal diffraction data). The carbonyl group is connected to the
imine group via an intramolecular hydrogen bond. The characteristic
region for the carbonyl stretching vibrations in thiourea derivatives is
1700–1650 cm−1 34–36 A strong absorption band at 1673–1689 cm−1 in
.
the IR spectra of the new compounds is ascribed to the stretching vi-
bration of the carbonyl group. A strong band at ∼1240 cm−1 is assigned
to the stretching vibration of the thiocarbonyl group. This results agree
with the data in the literature.37,38
The 1H NMR spectra of the new thioureas are consistent with their
structures. Here only the N-H signals are discussed. The two N-H
signals of the compounds 1–9 are observed at 12.00–12.42 and at
11.80–11.99 ppm. Because of the formation of an intramolecular hy-
drogen bond, the signal of the imine proton, which makes a hydrogen
bond, appears at a lower field.37 This observation agrees with the re-
sults of Li et al.38 The signal of the other imine proton appears at higher
field. Generally the NMR signals of NH protons for amides are observed
in the range of 9–10 ppm. The low-field shift of the signal for the imine
proton for compounds 1–9 can be attributed to the deshielding effect
of the electron-withdrawing carbonyl and thiocarbonyl group. All these

˘
D. S. Mansuroglu et al.
3224
FIGURE 1 Molecular structure of 4. Thermal ellipsoids are shown at the 50%
probability level.
data agree with the results of FT-IR ATR investigations and single
crystal X-ray diffraction.37,38
The
molecular
structure
of
N-(2,2-diphenylacetyl)-Nꢀ-(4-
chlorophenyl) thiourea is depicted in Figure 1. Selected bond lengths
and angles are presented in Table I. All C-C bond lengths and angles
of 4 are in the normal ranges.39 The geometry of the central carbonyl
thiourea group is also in agreement with those observed in substituted
thiourea derivatives.32,33,40,41 The bond lengths of the carbonyl and
thiocarbonyl groups in 4 are typical for double bonds, C8-O1 = 1.223(2)
Å, C7-S1 = 1.6588(19) Å. The C-N bond lengths [N1-C8 = 1.370(2)
Å, N1-C7 = 1.401(3) Å, N2-C7 = 1.335(3) Å, N2-C1 = 1.418(3) Å]
differ significantly from one another but are shorter as compared
with the typical value for a C-N single bond (1.479 Å).29,32,33,40–42 This
information indicates partial electron delocalization within the C8-
N1-C7-N2 fragment. The molecule adopts cis-trans configuration with
respect to the position of the 4-chlorophenyl and 2,2-diphenylacetyl
groups relative to the thiocarbonyl sulfur atom across the N1-C7
and N2-C7 bonds, respectively.40–42 The conformation of the molecule
with respect to the thiocarbonyl and carbonyl moieties is twisted,
as reflected by the torsion angles O1-C8-N1-C7, C8-N1-C7-N2, and
S1-C7-N1-C8 of 1.03◦, –5.75◦, and 173.09◦, respectively.31–33 The
maximum deviation from the O1-C8-N1-C7-N2 plane is 0.035(2) Å.

N-(2,2-Diphenylacetyl)-N ꢀ-Substituted Thiourea Derivatives
3225
TABLE I Selected Bond Lengths (Å) and Angles
(◦) of Compound 4
Bond Lengths
O1-C8
Cl1-C4
S1-C7
N1-C8
1.223(2)
1.738(2)
1.659(2)
1.370(2)
1.401(3)
N2-C7
N2-C1
C8-C9
C9-C10
C9-C16
1.335(3)
1.418(3)
1.526(3)
1.523(3)
1.526(3)
N1-C7
Bond Angles
C8-N1-C7
C7-N2-C1
N2-C7-N1
N2-C7-S1
N1-C7-S1
128.3(2)
O1-C8-N1
O1-C8-C9
N1-C8-C9
C10-C9-C16
C10-C9-C8
122.6(2)
128.2(2)
114.7(2)
126.7(2)
118.6(2)
122.2(2)
115.2(2)
113.3(2)
114.1(2)
However, the central carbonyl thiourea moiety (S1-C7-N1-N2-C8-O1)
connecting the 4-chlorophenyl and 2,2-diphenylacetyl groups is almost
planar, with atom O1 deviating by 0.070(2) Å. Intramolecular hydrogen
bonding N2-H2. . .O1, N-H 0.90 Å, H···O 1.87 Å, N-H···O 139◦ results
in the formation of a six-membered ring in the O1-C8-N1-C7-N2 plane
(Figure 2). This intramolecular hydrogen bonding will influence the
coordination behavior of the compounds. Thiourea derivatives such as
N,N-dialkyl-Nꢀ-benzoylthiourea easily coordinate to a metal atom via
both sulfur and oxygen atoms. However, for 4 and related compounds,
it will be difficult for the carbonyl oxygen atom to participate in
the coordination with transition metal atoms because it is involved
in intramolecular hydrogen bonding. In the crystal structure, the
molecules are linked by intermolecular hydrogen bonds: N1-H1···O1i,
with N-H 0.90 Å, H-O 2.02 Å, N-H-O 173◦ [symmetry code: (i) x,
1/2−y,1/2+z] (Figure 2).
EXPERIMENTAL
Instrumentation
The room temperature attenuated total reflection Fourier transform in-
frared (FT-IR ATR) spectra of all synthesized compounds were recorded
using a Varian FTS1000 FT-IR spectrometer with a Diamond/ZnSe
prism (4000–525 cm−1; number of scans: 250; resolution: 1 cm−1). All
1H NMR spectra were recorded with a Bruker DPX-400 spectrometer,
using CDCl3 as solvent and TMS as internal standard. C, H, and N anal-
yses were carried out with a Carlo Erba MOD 1106 elemental analyzer.
Melting points were determined on a digital melting point instrument

˘
D. S. Mansuroglu et al.
3226
FIGURE 2 Packing diagram for 4 in the crystal, with hydrogen bonds as
dotted lines; H atoms not involved are omitted.
(Electrothermal model 9200). Single crystal X-ray data were collected
on a Rigaku Mercury AFC8S system with a Mercury CCD detector
using graphite-monochromated MoKα radiation (λ = 0.71073 Å). The
structure was solved by direct methods and refined using full-matrix
least-squares techniques (on F2).43 Data were corrected for Lorentz and
polarization effects and for absorption. The latter correction was made
using REQABA, a multi-scan technique.44 All non-hydrogen atoms were
refined anisotropically. Further details concerning data collection and
refinement are given in Table II.
Synthesis of Compounds 1–9: General Procedure
All chemicals used for the preparation were of reagent grade quality.
Ethanol and acetone were distilled before use. The compounds were
prepared by a procedure similar to that reported in the literature.31–33
A solution of 2,2-diphenylacetyl chloride (0.005 mol) in acetone (50 mL)
was added dropwise to a suspension of potassium thiocyanate (0.005
mol) in acetone (50 mL). The reaction mixture was heated (35◦C) under
reflux for 30 min and then cooled to room temperature. A solution of

N-(2,2-Diphenylacetyl)-N ꢀ-Substituted Thiourea Derivatives
3227
TABLE II Crystallographic Data and Refinement Pa-
rameters for Compound 4
Empirical formula
Formula weight
Temperature (K)
Wavelength (Å)
Crystal system
Space group
Unit cell dimensions
a (Å)
C21H17ClN2OS
380.88
153(2)
0.71073
Monoclinic
P21/c
9.6551(19)
b (Å)
20.060(4)
c (Å)
9.894(2)
104.29(3)
β (◦)
V (Å3)
1857.0(6)
Z
4
Dc (g/cm3)
1.362
0.330
792
0.36 × 0.29 × 0.19
3.54 to 25.70
−11 ≤ h ≤ 11
−23 ≤ k ≤ 23
−9 ≤ l ≤ 11
11273
Absorption coefficient (mm−1
F(000)
)
Crystal size (mm3)
θ range for data collection (◦)
Index ranges
Reflections collected
Independent reflections (Rint
Absorption correction
Refinement method
Data/parameters
)
3280 (0.029)
Multi scan
Full-matrix least-squares on F2
3280/235
Goodness-of-fit on F2
1.065
Final R indices [I>2sigma(I)]
R indices (all data)
R1 = 0.0394, wR2 = 0.0941
R1 = 0.0544, wR2 = 0.1035
0.370 and −0.470
Largest diff. peak and hole (e.Å−3
)
the primary amine (0.005 mol) in acetone (30 mL) was added to the
mixture during a period of 15 min at room temperature and stirred
for 2 h. Hydrochloric acid (0.1 N, 300 mL) was added, and the solution
was filtered. The solid product was washed with water and purified by
recrystallization from ethanol:dichloromethane mixture (1:1).
N-(2,2-Diphenylacetyl)-N ꢀ-phenylthiourea (1)
White solid. Yield: 87% (1.5071 g). Mp: 160–162◦C. Anal. Calcd for
C21H18N2OS: C 72.8; H 5.2; N 8.1. Found: C 72.4; H 5.2; N 8.0%. FT-IR
(cm−1): ν(N-H) 3254, 3179 (v), ν(C-H) 3061–3032 (v), ν(C=O) 1679 (s),
1
ν(C=S) 1235 (s). H NMR (CDCl3): δ = 12.35 (s, 1H, CSNH), 11.85 (s,
1H, CONH), 7.65–7.23 (m, 15H, arom-H), 5.49 (s, 1H, CH).

˘
D. S. Mansuroglu et al.
3228
N-(2,2-Diphenylacetyl)-N ꢀ-(2-chlorophenyl)-thiourea (2)
White solid. Yield: 85% (1.6188 g). Mp: 134–136◦C. Anal. Calcd for
C21H17N2OSCl: C 66.2; H 4.5; N 7.4. Found: C 66.1; H 4.5; N 7.3%. FT-
IR (cm−1): ν(N-H) 3262, 3212 (v), ν(C-H) 3060–3027 (v), ν(C=O) 1676
(s), ν(C=S) 1239 (s). 1H NMR (CDCl3): δ = 12.33 (s, 1H, CSNH), 11.99
(s, 1H, CONH), 8.01–7.28 (m, 14H, arom-H), 5.50 (s, 1H, CH).
N-(2,2-Diphenylacetyl)-N ꢀ-(3-chlorophenyl)-thiourea (3)
White solid. Yield: 90% (1.7140 g). Mp: 165–167◦C. Anal. Calcd for
C21H17N2OSCl: C 66.2; H 4.5; N 7.4. Found: C 66.1; H 4.5; N 7.2%. FT-
IR (cm−1): ν(N-H) 3252, 3168 (v), ν(C-H) 3056–3022 (v), ν(C=O) 1677
(s), ν(C=S) 1239 (s). 1H NMR (CDCl3): δ = 12.36 (s, 1H, CSNH), 11.90
(s, 1H, CONH), 7.89–7.30 (m, 14H, arom-H), 5.48 (s, 1H, CH).
N-(2,2-Diphenylacetyl)-N ꢀ-(4-chlorophenyl)-thiourea (4)
White solid. Yield: 88% (1.6759 g). Mp: 135–137◦C. Anal. Calcd for
C21H17N2OSCl: C 66.2; H 4.5; N 7.4. Found: C 65.9; H 4.4; N 7.3%. FT-
IR (cm−1): ν(N-H) 3264, 3156 (v), ν(C-H) 3064–3020 (v), ν(C=O) 1677
(s), ν(C=S) 1247 (s). 1H NMR (CDCl3): δ = 12.30 (s, 1H, CSNH), 11.90
(s, 1H, CONH), 7.66–7.28 (m, 14H, arom-H), 5.48 (s, 1H, CH).
N-(2,2-Diphenylacetyl)-N ꢀ-(2-methylphenyl)-thiourea (5)
White solid. Yield: 87% (1.5680 g). Mp: 138–140◦C. Anal. Calcd for
C22H20N2OS: C 73.3; H 5.6; N 7.8. Found: C 73.0; H 5.5; N 7.7%. FT-IR
(cm−1): ν(N-H) 3254, 3182 (v), ν(C-H) 3060–3032 (v), ν(C=O) 1673 (s),
1
ν(C=S) 1243 (s). H NMR (CDCl3): δ = 12.00 (s, 1H, CSNH), 11.86 (s,
1H, CONH), 7.55–7.19 (m, 14H, arom-H), 5.49 (s, 1H, CH), 2.19 (s, 3H,
CH3).
N-(2,2-Diphenylacetyl)-N ꢀ-(4-methylphenyl)-thiourea (6)
White solid. Yield: 90% (1.6221 g). Mp: 173–175◦C. Anal. Calcd for
C22H20N2OS: C 73.3; H 5.6; N 7.8. Found: C 73.2; H 5.5; N 7.6%. FT-IR
(cm−1): ν(N-H) 3258, 3162 (v), ν(C-H) 3054–3031 (v), ν(C=O) 1677 (s),
1
ν(C=S) 1243 (s). H NMR (CDCl3): δ = 12.30 (s, 1H, CSNH), 11.80 (s,
1H, CONH), 7.50–7.17 (m, 14H, arom-H), 5.49 (s, 1H, CH), 2.28 (s, 3H,
CH3).
N-(2,2-Diphenylacetyl)-N ꢀ-(3-methoxyphenyl)-thiourea (7)
White solid. Yield: 89% (1.6753 g). Mp: 140–142◦C. Anal. Calcd for
C22H20N2O2S: C 70.2; H 5.4; N 7.4. Found: C 70.2; H 5.3; N 7.4%. FT-IR
(cm−1): ν(N-H) 3271, 3187 (v), ν(C-H) 3061–3029 (v), ν(C=O) 1682 (s),
1
ν(C=S) 1264 (s). H NMR (CDCl3): δ = 12.39 (s, 1H, CSNH), 11.86 (s,

N-(2,2-Diphenylacetyl)-N ꢀ-Substituted Thiourea Derivatives
3229
1H, CONH), 7.40–7.18 (m, 14H, arom-H), 5.49 (s, 1H, CH), 3.45 (s, 3H,
CH3).
N-(2,2-Diphenylacetyl)-N ꢀ-(4-methoxyphenyl)-thiourea (8)
White solid. Yield: 91% (1.7129 g). Mp: 143–145◦C. Anal. Calcd for
C22H20N2O2S: C 70.2; H 5.4; N 7.4. Found: C 70.2; H 5.3; N 7.3%. FT-IR
(cm−1): ν(N-H) 3237, 3181 (v), ν(C-H) 3058–3030 (v), ν(C=O) 1676 (s),
1
ν(C=S) 1251 (s). H NMR (CDCl3): δ = 12.30 (s, 1H, CSNH), 11.80 (s,
1H, CONH), 7.50–7.17 (m, 14H, arom-H), 5.48 (s, 1H, CH), 2.28 (s, 3H,
CH3).
N-(2,2-Diphenylacetyl)-N ꢀ-(naphthalen-1-yl)-thiourea (9)
White solid. Yield: 94% (1.8636 g). Mp: 180–182◦C. Anal. Calcd for
C25H20N2OS: C 75.7; H 5.1; N 7.1. Found: C 75.3; H 5.1; N 7.0%. FT-IR
(cm−1): ν(N-H) 3228, 3192 (v), ν(C-H) 3061–3018 (v), ν(C=O) 1689 (s),
1
ν(C=S) 1243 (s). H NMR (CDCl3): δ = 12.42 (s, 1H, CSNH), 11.99 (s,
1H, CONH), 7.99–7.31 (m, 17H, arom-H), 5.57 (s, 1H, CH).
Supplementary Material
Crystallographic data for the structure reported in this article have
been deposited at the Cambridge Crystallographic Data Centre (CCDC)
with quotation number CCDC-662387 for compound 4 and can be ob-
tained free of charge on application to CCDC 12 Union Road, Cam-
bridge CB2 1EZ, UK [Fax: (internat.) + 44(1223)336–033, E-mail: de-
posit@ccdc.cam.ac.uk].
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