IFLP   13074
INSTITUTO DE FISICA LA PLATA
Unidad Ejecutora - UE
artículos
Título:
Competing intramolecular NAH...C hydrogen bonds and extended intermolecular network in 1-(4-chlorobenzoyl)-3-(2-methyl-4- oxopentan-2-yl) thiourea analyzed by experimental and theoretical methods
Autor/es:
AAMER SAEED; ASMA KHURSHID; JERRY P. JASINSKI; C. GUSTAVO POZZI; ADOLFO C. FANTONI; MAURICIO F. ERBEN
Revista:
CHEMICAL PHYSICS
Editorial:
ELSEVIER SCIENCE BV
Referencias:
Lugar: Amsterdam; Año: 2014 vol. 431 p. 39 - 46
ISSN:
0301-0104
Resumen:
Abstract
The synthesis of a novel 1-acyl-thiourea species (C14H17N2O2SCl),
has been tailored in such a way that two distinct N?H···O=C intramolecular competing
hydrogen bonds are feasible. The X-ray structure analysis as well as the
vibrational (FT-IR and FT-Raman) data reveal that the S conformation is
preferred, with the C=O and C=S bonds of the acyl-thiourea group pointing in
opposite directions. The preference for the intramolecular N2?H···O1=C7
hydrogen bond within the ?C(O)NHC(S)NH? core is confirmed. The Natural Bond
Orbital and the Atom in Molecule approaches demonstrate that a strong hyperconjugative lpO1→ s*(N2?H) remote
interaction between the acyl and the thioamide N2?H groups is responsible for
the stabilization of the S
conformation. Intermolecular
interactions have been characterized in the periodic system electron density and
the topological analysis reveals the presence of an extended
intermolecular network in the crystal, including a Cl∙∙∙N interaction playing a
relevant role in crystal packing.