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. 2010

Juan Z Dávalos, and Maria das Dores M C Ribeiro da Silva, and Manuel A V Ribeiro da Silva, and Vera L S Freitas, and Pilar Jiménez, and Maria Victoria Roux, and Pilar Cabildo, and Rosa M Claramunt, and José Elguero
Instituto de Química Física Rocasolano, CSIC, Serrano, 119, E-28006 Madrid, Spain. jdavalos@iqfr.csic.es

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(f)H(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.

UI MeSH Term Description Entries
D008782 Methylurea Compounds Urea compounds which are substituted with one or more methyl groups. Compounds, Methylurea
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D010671 Phenylurea Compounds Compounds that include the amino-N-phenylamide structure. Phenylcarbamides,Phenylurea Derivatives,Compounds, Phenylurea,Derivatives, Phenylurea
D011789 Quantum Theory The theory that the radiation and absorption of energy take place in definite quantities called quanta (E) which vary in size and are defined by the equation E Quantum Theories,Theories, Quantum,Theory, Quantum
D002224 Carbanilides Compounds consisting of two phenyl groups joined by a urea. Derivatives may be used as ANTIPARASITIC AGENTS. Diphenylurea Compounds,Compounds, Diphenylurea
D006827 Hydantoins Compounds based on imidazolidine dione. Some derivatives are ANTICONVULSANTS. Hydantoin,Imidazolidine-2,4-Diones,Imidazolidine 2,4 Diones
D001462 Barbital A long-acting barbiturate that depresses most metabolic processes at high doses. It is used as a hypnotic and sedative and may induce dependence. Barbital is also used in veterinary practice for central nervous system depression. Barbitone,Diethylmalonylurea,Ethylbarbital,Diemal,Dormileno,Medinal,Veronal
D013696 Temperature The property of objects that determines the direction of heat flow when they are placed in direct thermal contact. The temperature is the energy of microscopic motions (vibrational and translational) of the particles of atoms. Temperatures
D013816 Thermodynamics A rigorously mathematical analysis of energy relationships (heat, work, temperature, and equilibrium). It describes systems whose states are determined by thermal parameters, such as temperature, in addition to mechanical and electromagnetic parameters. (From Hawley's Condensed Chemical Dictionary, 12th ed) Thermodynamic

Related Publications

Juan Z Dávalos, and Maria das Dores M C Ribeiro da Silva, and Manuel A V Ribeiro da Silva, and Vera L S Freitas, and Pilar Jiménez, and Maria Victoria Roux, and Pilar Cabildo, and Rosa M Claramunt, and José Elguero
August 1974, The Journal of pharmacology and experimental therapeutics,
Juan Z Dávalos, and Maria das Dores M C Ribeiro da Silva, and Manuel A V Ribeiro da Silva, and Vera L S Freitas, and Pilar Jiménez, and Maria Victoria Roux, and Pilar Cabildo, and Rosa M Claramunt, and José Elguero
April 2011, Advanced synthesis & catalysis,
Juan Z Dávalos, and Maria das Dores M C Ribeiro da Silva, and Manuel A V Ribeiro da Silva, and Vera L S Freitas, and Pilar Jiménez, and Maria Victoria Roux, and Pilar Cabildo, and Rosa M Claramunt, and José Elguero
June 2009, Organic letters,
Juan Z Dávalos, and Maria das Dores M C Ribeiro da Silva, and Manuel A V Ribeiro da Silva, and Vera L S Freitas, and Pilar Jiménez, and Maria Victoria Roux, and Pilar Cabildo, and Rosa M Claramunt, and José Elguero
October 2001, Chemistry (Weinheim an der Bergstrasse, Germany),
Juan Z Dávalos, and Maria das Dores M C Ribeiro da Silva, and Manuel A V Ribeiro da Silva, and Vera L S Freitas, and Pilar Jiménez, and Maria Victoria Roux, and Pilar Cabildo, and Rosa M Claramunt, and José Elguero
January 1980, The Journal of pharmacology and experimental therapeutics,
Juan Z Dávalos, and Maria das Dores M C Ribeiro da Silva, and Manuel A V Ribeiro da Silva, and Vera L S Freitas, and Pilar Jiménez, and Maria Victoria Roux, and Pilar Cabildo, and Rosa M Claramunt, and José Elguero
September 2002, Chemical communications (Cambridge, England),
Juan Z Dávalos, and Maria das Dores M C Ribeiro da Silva, and Manuel A V Ribeiro da Silva, and Vera L S Freitas, and Pilar Jiménez, and Maria Victoria Roux, and Pilar Cabildo, and Rosa M Claramunt, and José Elguero
October 2022, Dalton transactions (Cambridge, England : 2003),
Juan Z Dávalos, and Maria das Dores M C Ribeiro da Silva, and Manuel A V Ribeiro da Silva, and Vera L S Freitas, and Pilar Jiménez, and Maria Victoria Roux, and Pilar Cabildo, and Rosa M Claramunt, and José Elguero
February 2017, Molecular diversity,
Juan Z Dávalos, and Maria das Dores M C Ribeiro da Silva, and Manuel A V Ribeiro da Silva, and Vera L S Freitas, and Pilar Jiménez, and Maria Victoria Roux, and Pilar Cabildo, and Rosa M Claramunt, and José Elguero
December 2023, International journal of molecular sciences,
Juan Z Dávalos, and Maria das Dores M C Ribeiro da Silva, and Manuel A V Ribeiro da Silva, and Vera L S Freitas, and Pilar Jiménez, and Maria Victoria Roux, and Pilar Cabildo, and Rosa M Claramunt, and José Elguero
January 1967, Voprosy meditsinskoi khimii,
Copied contents to your clipboard!