Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/10736
Title: Oxygen-by-sulfur substitutions in glycine: conformational and vibrational effects
Authors: Carvalho, Luís A. E. Batista de 
Marques, M. Paula M. 
Teixeira-Dias, José J. C. 
Issue Date: 1999
Publisher: Royal Society of Chemistry
Citation: Perkin Transactions 2. (1999) 2507-2514
Abstract: Molecular geometries, energies, dipole moments and atomic charges of several conformations of glycine (NH2CH2C(O)OH) and its oxygen-by-sulfur substituted analogues (NH2CH2C(O)SH, NH2CH2C(S)OH and NH2CH2C(S)SH) were determined by ab initio MO calculations at the MP2/6-31G** level, and vibrational frequencies, infrared and Raman intensities were evaluated within the harmonic approximation, at the HF/6-31G** level. Profiles for the potential energy and several geometric parameters as a function of the NC–C(X) (X = O, S) dihedral angle (C–C internal rotation) were obtained using the 3-21G(N*) basis set. Conformational and vibrational effects of oxygen-by-sulfur substitutions are discussed. In particular, the occurrence of intramolecular close contacts between the NH2CH2– and –C(X)YH (X, Y = O or S) moieties of the molecule is considered, for some of the most stable conformations of each analogue. As a general trend, the results clearly point to the stabilisation of the G/anti forms (:NCC 60°, NCCX 180°), highlighting the importance of the N:· · ·H(Y) and N:· · ·S(H) interactions, e.g. in conformers G/anti/s-trans for the thione form (X = S) and G/anti/s-cis for the thiol one (Y = S), respectively.
URI: http://hdl.handle.net/10316/10736
ISSN: 0300-9580
DOI: 10.1039/a905073f
Rights: openAccess
Appears in Collections:FCTUC Ciências da Vida - Artigos em Revistas Internacionais
FCTUC Química - Artigos em Revistas Internacionais

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