Stereochemical behavior of (1)J(CH) and (2)J(CH) NMR coupling constants in alpha-substituted acetamides

Author(s)

Pedersoli, Susimaire ^[1] ; Tormena, Claudio F. ^[1] ; dos Santos, Francisco P. ^[1] ; Contreras, Ruben H. ^{[2, 3]} ; Rittner, Roberto ^[1]

Affiliation

^[1] Univ Estadual Campinas, Inst Chem, Phys Organ Chem Lab, BR-13084971 Campinas, SP - Brazil

^[2] Consejo Nacl Invest Cient & Tecn, RA-1033 Buenos Aires, DF - Argentina

^[3] Univ Buenos Aires, FCEyN, Dept Phys, Buenos Aires, DF - Argentina

• Document type: Journal article
• Source: Journal of Molecular Structure; v. 891, n. 1-3, p. 508-513, NOV 26 2008.
• Web of Science Citations: 6

Abstract

A rationalization of the stereochemical behavior of (1)J(CH) and (2)J(CH) coupling constants, involving nuclei in the vicinity of a carbonyl group were carried out in fluoroacetamide (1), chloroacetamide (2), bromoacetamide (3) and cyanoacetamide (4). (1)J(CH) and (2)J(CH) experimental and theoretically calculated coupling constant together with a qualitative analyses of hyperconjugative interactions through NBO data, showed that observed behavior is mainly due to the hyperconjugative interactions and electrostatic effects. (C) 2008 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 05/59649-0 - Conformational equilibria studies by nuclear magnetic resonance spectroscopy, infrared spectroscopy and theoretical calculations
• Grantee: Roberto Rittner Neto
• Support Opportunities: Research Projects - Thematic Grants