On the role of inter- and intramolecular interactions on the molecular structure and conformational properties of 1-(2-chlorobenzoyl)thiourea. An experimental and theoretical approach

SAEED, AAMER; KHURSHID, A.; BOLTE, MICHAEL; FANTONI, ADOLFO; ERBEN, MAURICIO FEDERICO

SPECTROCHIMICA ACTA. PART A, MOLECULAR AND BIOMOLECULAR SPECTROSCOPY.

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2015 vol. 143 p. 59 - 66

1386-1425

The vibrational analysis (FT-IR and FT-Raman) for the new 1-(2-chlorobenzoyl)thiourea species suggeststhat strong intramolecular interactions affect the conformational properties. The X-ray structure determinationcorroborates that an intramolecular N-H···O=C hydrogen bond occurs between the carbonyl(?C=O) and thioamide (?NH2) groups. Moreover, periodic system electron density and topological analysis have been applied to characterize the intermolecular interactions in the crystal. Extended N-H···S=C hydrogen-bonding networks between both the thioamide (N-H) and carbamide (NH2) groups and the thiocarbonyl bond (C=S) determine the crystal packing. The Natural Bond Orbital (NBO) population analysis demonstrates that strong hyperconjugative remote interactions are responsible for both, intra and intermolecular interactions. The Atom in Molecule (AIM) results also show that the N-H···Clintramolecular hydrogen bond between the 2-Cl-phenyl ring and the amide group characterized in the free molecule changes to an N···Cl interaction as a consequence of crystal packing.