caa a22 4500 469072091 CHVBK 20180323132924.0 cr unu---uuuuu 170328e19921201xx s 000 0 eng 10.1007/BF00672012 doi (NATIONALLICENCE)springer-10.1007/BF00672012 Ab initio study of the structure and tautomerism of internally hydrogen-bonded aromatic carbonyls: Salicylamide, salicylic Acid, and O-hydroxybenzoyl cyanide [Elektronische Daten] [Carlos Estévez, Miguel Ríos, Jesús Rodríguez] We carried out an ab initio study at the 3-21 G level with full geometric optimization of three compounds with intramolecular hydrogen bonds in their most stable conformations, namely salicylamide, salicylic acid, ando-hydroxybenzoyl cyanide. The energy of the hydrogen bonds was estimated and their structural effects were analyzed. We also studied the stability of the tautomers resulting from a proton transfer between the oxygen atoms by analyzing the potential surfaces of the tautomerization process. The potential surfaces of salicylamide and salicylic acid showed a single minimum, while that of the cyanide showed a double minimum with a scarcely significant inverse barrier (3.01 kJ/mol). Single point calculations at the 6-31+G* level on salicylic acid showed a trend to appear a second minimum in the potential surface. Both the strength of the hydrogen bond and the occurrence of stable tautomers were found to be clearly correlated with the electron-releasing and electron-withdrawing ability of the organic functions present in each compound (-NH2,-OH and -CN, respectively). Plenum Publishing Corporation, 1992 Estévez Carlos Departamento de Química Física, Facultad de Química, Universidad de Santiago de Compostela, 15706, Santiago de Compostela, Galicia, Spain aut Ríos Miguel Departamento de Química Física, Facultad de Química, Universidad de Santiago de Compostela, 15706, Santiago de Compostela, Galicia, Spain aut Rodríguez Jesús Departamento de Química Física, Facultad de Química, Universidad de Santiago de Compostela, 15706, Santiago de Compostela, Galicia, Spain aut Structural Chemistry Kluwer Academic Publishers 3/6(1992-12-01), 381-387 1040-0400 3:6<381 1992 3 11224 https://doi.org/10.1007/BF00672012 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00672012 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Estévez Carlos Departamento de Química Física, Facultad de Química, Universidad de Santiago de Compostela, 15706, Santiago de Compostela, Galicia, Spain aut NATIONALLICENCE 700 1- Ríos Miguel Departamento de Química Física, Facultad de Química, Universidad de Santiago de Compostela, 15706, Santiago de Compostela, Galicia, Spain aut NATIONALLICENCE 700 1- Rodríguez Jesús Departamento de Química Física, Facultad de Química, Universidad de Santiago de Compostela, 15706, Santiago de Compostela, Galicia, Spain aut NATIONALLICENCE 773 0- Structural Chemistry Kluwer Academic Publishers 3/6(1992-12-01), 381-387 1040-0400 3:6<381 1992 3 11224 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer