Computational Thermochemistry of Six Ureas, Imidazolidin-2-one, N,N '-Trimethyleneurea, Benzimidazolinone, Parabanic Acid, Barbital (5,5 '-Diethylbarbituric Acid), and 3,4,4 '-Trichlorocarbanilide, with an Extension to Related Compounds

• Type: Article in International Scientific Journal
• Date: 2010

Authors

Juan Z Davalos (Author) Other; Maria das Dores C R Ribeiro da Silva (Author) FCUP; Manuel A V R Ribeiro da Silva (Author) FCUP; Vera L S Freitas (Author) Other; Pilar Jimenez (Author) Other; Maria Victoria Roux (Author) Other; Pilar Cabildo (Author) Other; Rosa M Claramunt (Author) Other; Jose Elguero (Author) Other

Journal

Title: Journal of Physical Chemistry A

Vol. 114

Pages: 9237-9245

ISSN: 1089-5639

Publisher: American Chemical Society

Indexing

ISI Web of Knowledge - 20 Citations

Scopus - 19 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

CORDIS: Physical sciences > Chemistry > Physical chemistry

Other information

Authenticus ID: P-003-2Y2

DOI: 10.1021/jp103514f

Abstract (EN): A computational study of the structural and thermochemical properties of N-phenyl (open) and N-alkyl (cyclic) ureas, through the use of M05-2X and B3LYP density functional theory calculations has been carried out. The consistency of the literature experimental results has been confirmed, and using mainly isodesmic reactions, the unknown Delta fH(0)(g) of the other urea derivatives were estimated. The experimental results together with the theoretical information have permitted the study of the effect of phenyl, p- and m-chlorophenyl, alkyl, and carbonyl substitutions on the thermodynamical stability of urea and its cyclic derivatives. The peculiar behavior of the N-tert-butyl substituent in cyclic ureas has been related to geometric deformations.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 9