Online citations, reference lists, and bibliographies.
← Back to Search

A Quantum Mechanical Study Of The Stability And Structural Properties Of Substituted Acylthiourea Compounds

M. G. Woldu, J. Dillen
Published 2008 · Chemistry

Cite This
Download PDF
Analyze on Scholarcy
Share
The conformational, structural and electronic properties of eight acylthiourea derivatives with the general form N-acyl-N′, N′-alkylthiourea have been investigated computationally at the MP2 level of theory and the 6-311G(d) basis set. Transition states between the four stable conformations were identified and characterized. There is a good correlation between the electron density at the bond critical point of each of the three C–N bonds present in the molecules, the calculated bond length, and the rotational barrier around these bonds. The calculations suggest the C(S)-N′ bond to have considerable double bond character which, according to analysis in terms of the Natural Bond Orbitals paradigm, can be attributed to a more favorable delocalization of the N′ lone pair into the antibonding π*(C=S) orbital than the lone pair on the other nitrogen. The influence of the various substituents on the structural and energetic features of the acylthiourea backbone is also investigated.
This paper references
10.1021/JA01402A019
THE SIZES OF IONS AND THE STRUCTURE OF IONIC CRYSTALS
L. Pauling (1927)
10.1021/J100866A055
Barriers to internal rotation in thioamides. Experimental results and molecular orbital calculations
J. Sandstrom (1967)
10.1002/(SICI)1096-987X(19980430)19:6<593::AID-JCC3>3.0.CO;2-M
Natural resonance theory: I. General formalism
E. Glendening (1998)
10.1039/B205056K
Anti-tumour platinum acylthiourea complexes and their interactions with DNA
A. Rodger (2002)
10.1002/(SICI)1096-987X(19980430)19:6<628::AID-JCC5>3.0.CO;2-T
Natural resonance theory: III. Chemical applications
E. Glendening (1998)
10.1063/1.466360
From concepts to algorithms for the characterization of reaction mechanisms. H2CS as a case study
C. Minichino (1994)
10.1107/S1600536806039614
N,N-Di-n-butyl-N′-pivaloylthiourea
J. Dillen (2006)
10.1016/S0277-5387(00)00419-8
Synthesis and characterisation of mixed-ligand platinum(II)–sulfoxide complexes, [PtCl(DMSO)(L)], for potential use as chemotherapeutic agents (HL=N,N-dialkyl-N′-(3-R-benzoyl)thiourea)
C. Sacht (2000)
10.1016/S0040-4039(02)01754-9
Efficient solution phase synthesis of 2-(N-acyl)-aminobenzimidazoles
P. Seth (2002)
10.1002/CBER.187300601186
Zur Kenntniss des Sulfoharnstoffs
M. Nencki (1873)
10.1021/JA01379A006
THE PRINCIPLES DETERMINING THE STRUCTURE OF COMPLEX IONIC CRYSTALS
L. Pauling (1929)
10.1007/BF00761472
Electronic structure and vibrational spectrum of acetylthiocarbamide
S. A. Slivko (1993)
10.1002/ZAAC.200400030
Cis‐trans Isomerism in Copper(II) Complexes with N‐acyl Thiourea Ligands
Wilfredo Hernández (2004)
10.1039/B509727D
Doubly-linked 1D coordination polymers derived from 2 ∶ 2 metallamacrocyclic Ni(II) complexes with bipodal acylthiourea and exo-bidentate N-donor bridging ligands: toward potentially selective chemical sensors?
Oren Hallale (2005)
10.1063/1.445134
Natural bond orbital analysis of near‐Hartree–Fock water dimer
A. Reed (1983)
10.1063/1.438959
Reaction path Hamiltonian for polyatomic molecules
W. Miller (1980)
10.1039/B603802F
Competitive bulk liquid membrane transport and solvent extraction of some transition and post-transition metal ions using acylthiourea ligands as ionophores
Michael M. Habtu (2006)
10.1063/1.467880
CHARACTERIZATION OF THE POTENTIAL ENERGY SURFACE OF THE HO2 MOLECULAR SYSTEM BY A DENSITY FUNCTIONAL APPROACH
V. Barone (1994)
10.1021/TX700270R
A rational chemical intervention strategy to circumvent bioactivation liabilities associated with a nonpeptidyl thrombopoietin receptor agonist containing a 2-amino-4-arylthiazole motif.
A. Kalgutkar (2007)
10.1016/0009-2614(90)87217-F
Ab initio calculation of anharmonic constants for a transition state, with application to semiclassical transition state tunneling probabilities
W. Miller (1990)
10.1063/1.454172
On evaluating the reaction path Hamiltonian
M. Page (1988)
10.1002/MRC.1270130603
Application of 15N spectroscopy and dynamic NMR to the study of ureas, thioureas and their lewis acid adducts
M. Martín (1980)
10.1023/A:1022424228462
Bond Length–Electron Density Relationships: From Covalent Bonds to Hydrogen Bond Interactions
I. Alkorta (1998)
10.1021/CC020109Y
Solid phase synthesis and application of trisubstituted thioureas.
A. Katritzky (2003)
10.1016/S0022-2860(01)00626-3
Conformational analysis of 3,3-disubstituted benzoylthioureas using X-ray diffraction and ab initio calculations
M. Sosa-Albertus (2001)
10.1063/1.449486
Natural population analysis
A. Reed (1985)
10.1016/0166-1280(94)03862-F
From concepts to algorithms for the treatment of large amplitude internal motions and unimolecular reactions
V. Barone (1995)
10.1021/ar00109a003
Atoms In Molecules
R. Bader (1990)
10.1016/J.BMCL.2005.09.033
A novel class of potent influenza virus inhibitors: polysubstituted acylthiourea and its fused heterocycle derivatives.
C. Sun (2006)
10.1002/1521-3749(200201)628:1<41::AID-ZAAC41>3.0.CO;2-Q
Synthesen und Strukturen von N-Acylthioharnstoffkomplexen des Zinks und des Cadmiums
Martina Reinel (2002)
10.1016/0301-0104(90)87051-C
A systematic study of molecular vibrational anharmonicity and vibration-rotation interaction by self-consistent-field higher-derivative methods. Linear polyatomic molecules
W. Allen (1990)
Atoms in molecules : a quantum theory
R. Bader (1990)
10.1155/BCA.2005.299
Synthesis, Characterization And Antitumor Activity Of Copper(II) Complexes, [CuL2] [HL1-3=N,N-Diethyl-N'-(R-Benzoyl)Thiourea (R=H, o-Cl and p-NO2)]
Wilfredo Hernández (2005)
The Nature Of The Chemical Bond
L. Pauling (1939)
10.1021/JA00238A005
Theoretical analysis of hydrocarbon properties. 2. Additivity of group properties and the origin of strain energy
K. Wiberg (1987)
10.1016/S0014-827X(03)00132-0
Synthesis of N-substituted-N-acylthioureas of 4-substituted piperazines endowed with local anaesthetic, antihyperlipidemic, antiproliferative activities and antiarrythmic, analgesic, antiaggregating actions.
A. Ranise (2003)
10.1063/1.459634
Following steepest descent reaction paths. The use of higher energy derivatives with ab initio electronic structure methods
M. Page (1990)
10.1155/S1565363303000219
Synthesis, Characterization and Antitumor Activity of cis-bis(acylthioureato) platinum(II) Complexes, cis-[PtL2] [HL1=N,N-Diphenyl-N'-Benzoylthiourea or HL2=N,N-diphenyl-N'-(p-nitrobenzoyl)thiourea]
Wilfredo Hernández (2003)
10.1107/S0108768102003890
The Cambridge Structural Database: a quarter of a million crystal structures and rising.
F. Allen (2002)
10.1055/S-2004-829127
Synthesis of Mono- and N,N-Disubstituted Thioureas and N-Acylthioureas
A. R. Katritzky (2004)
10.1021/JP073974N
An evaluation of harmonic vibrational frequency scale factors.
J. P. Merrick (2007)
10.1021/JA00544A007
Natural hybrid orbitals
J. Foster (1980)
10.1021/JA01315A105
The Dependence of Interatomic Distance on Single Bond-Double Bond Resonance1
L. Pauling (1935)
10.1016/S0040-4020(00)00039-9
Alkylation of Benzoyl and Furoylthioureas as Polydentate Systems
A. M. Plutín (2000)
10.1016/S0010-8545(01)00337-X
New chemistry with old ligands: N-alkyl- and N,N-dialkyl-N′-acyl(aroyl)thioureas in co-ordination, analytical and process chemistry of the platinum group metals
K. Koch (2001)
10.1039/b211885h
Tailoring hydrophilic N,N-dialkyl-N?-acylthioureas suitable for Pt(ii), Pd(ii) and Rh(iii) chloride pre-concentration from acid aqueous solutions, and their complex separation by reversed-phase HPLCBased on the presentation given at Dalton Discussion No. 5, 10?12th April 2003, Noordwijkerhout, The N
Alpheus N. Mautjana (2003)
10.1021/JM0506423
Identification of potent and selective inhibitors of PDGF receptor autophosphorylation.
T. Furuta (2006)
10.1002/(SICI)1096-987X(19980430)19:6<610::AID-JCC4>3.0.CO;2-U
Natural resonance theory: II. Natural bond order and valency
E. Glendening (1998)
10.1246/BCSJ.55.3612
Infrared spectra and conformation of N-acetylthiourea.
S. Aruna (1982)



This paper is referenced by
10.1016/J.POLY.2018.02.016
Novel complexes possessing Hg–(Cl, Br, I)⋯OC halogen bonding and unusual Hg2S2(Br/I)4 kernel. The usefulness of τ4′ structural parameter
D. Rosiak (2018)
10.1016/j.molstruc.2020.128227
Conformational and crystal structure of acyl thiourea compounds: The case of the simple (2,2-dimethyl-propionyl) thiourea derivative
D. González (2020)
10.1107/S2053229616019495
Crystallographic study of self-organization in the solid state including quasi-aromatic pseudo-ring stacking interactions in 1-benzoyl-3-(3,4-dimethoxyphenyl)thiourea and 1-benzoyl-3-(2-hydroxypropyl)thiourea.
Andrzej Okuniewski (2017)
SINGLE MOLECULE AND SOLID STATE ENVIRONMENT STRUCTURAL CONFORMATIONS OF N-BENZOYL-N`-p-SUBSTITUTED PHENYLTHIOUREA: A COMPUTATIONAL STUDIES
Rafie Draman (2016)
10.1016/J.MOLSTRUC.2017.03.113
Synthesis, structural characterization and quantum chemical calculations on 1-(isomeric methylbenzoyl)-3-(4-trifluoromethylphenyl)thioureas
Lei Qiao (2017)
10.1016/j.jinorgbio.2015.04.008
Ru(II)-based complexes with N-(acyl)-N',N'-(disubstituted)thiourea ligands: Synthesis, characterization, BSA- and DNA-binding studies of new cytotoxic agents against lung and prostate tumour cells.
R. S. Correa (2015)
10.1016/J.CHEMPHYS.2014.01.009
Competing intramolecular NH⋯OC hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4-oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods
A. Saeed (2014)
10.1016/J.MOLSTRUC.2017.01.014
DFT and PCM-TD-DFT investigation of the electronic structures and spectra of 5-(3-phenyl-2-propenylidene)-2-thioxo-4-thiazolidinone derivatives
S. El-Taher (2017)
10.1002/EJIC.201600204
Organosilatranes with Acylthiourea Derivatives – Metal‐Ion Binding, Substituent‐Dependent Sensitivity, and Prospects for the Fabrication of Magnetic Hybrids
G. Singh (2016)
10.1016/J.MOLSTRUC.2015.07.049
Metal complexes of the nanosized ligand N-benzoyl-N′-(p-amino phenyl) thiourea: Synthesis, characterization, antimicrobial activity and the metal uptake capacity of its ligating resin
A. Elhusseiny (2015)
10.1016/J.CPLETT.2018.11.020
Acyl thiourea derivatives: A study of crystallographic, bonding, biological and spectral properties
E. Aguilar (2019)
10.1016/j.saa.2015.02.042
Intra- and intermolecular hydrogen bonding and conformation in 1-acyl thioureas: an experimental and theoretical approach on 1-(2-chlorobenzoyl)thiourea.
A. Saeed (2015)
10.1080/17415993.2013.834904
A review on the chemistry, coordination, structure and biological properties of 1-(acyl/aroyl)-3-(substituted) thioureas
A. Saeed (2014)
10.1016/J.POLY.2015.01.035
Coordination polymers and molecular structures among complexes of mercury(II) halides with selected 1-benzoylthioureas
Andrzej Okuniewski (2015)
10.1107/S2053229618015620
Copper(I) iodide ribbons coordinated with thiourea derivatives.
D. Rosiak (2018)
10.1021/jp806101t
Competition of hydrogen bonds and halogen bonds in complexes of hypohalous acids with nitrogenated bases.
I. Alkorta (2008)
10.1007/s11164-018-3596-5
Supramolecular self-assembly of new thiourea derivatives directed by intermolecular hydrogen bonds and weak interactions: crystal structures and Hirshfeld surface analysis
Ilkay Gumus (2018)
Semantic Scholar Logo Some data provided by SemanticScholar