Pyridinium-N-(2-pyridyl)aminides and related compounds: a theoretical study

被引:0
作者
Alkorta, Ibon [1 ]
Elguero, Jose [1 ]
机构
[1] CSIC, Inst Quim Med, Juan Cierva 3, E-28006 Madrid, Spain
关键词
Pyridinium-N-aminides; pyrazole; isoxazole; 1,2,3-triazole; furazan; B3LYP/6-31G*; MEP; AZINYLPYRIDINIUM N-AMINIDES; CAMBRIDGE STRUCTURAL DATABASE; REGIOSELECTIVE SYNTHESIS; CHEMISTRY; SALTS;
D O I
10.3998/ark.5550190.0012.308
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Seven families of pyridinium-N-(heteroaryl)aminides, both azinyl and azolyl, have been studied. For each family, three structures have been considered, the "classical" and two radicals. The transition states corresponding to the rotation of the pyridinium and the heterocycle were calculated at the B3LYP/6-31G* level.
引用
收藏
页码:99 / 113
页数:15
相关论文
共 30 条
[11]   PYRIDINIUM-N-(2-PYRIDYL)AMINIDES - A SELECTIVE APPROACH TO SUBSTITUTED 2-AMINOPYRIDINES [J].
CARCELLER, R ;
GARCIANAVIO, JL ;
IZQUIERDO, ML ;
ALVAREZBUILLA, J .
TETRAHEDRON LETTERS, 1993, 34 (12) :2019-2020
[12]   Crystalline organization and bonding of N-perfluoroacylpyridiniumaminides [J].
Caronna, T ;
Corradi, E ;
Meille, SV ;
Novo, B ;
Resnati, G ;
Sidoti, G .
JOURNAL OF FLUORINE CHEMISTRY, 1999, 97 (1-2) :183-190
[13]   Pd-catalyzed reactions on pyridinium N-heteroarylaminides. Step-by-step synthesis of 3,5-unsymmetrically disubstituted 2-aminopyridines [J].
Cordoba, Marta ;
Castillo, Rafael R. ;
Luisa Izquierdo, M. ;
Alvarez-Builla, Julio .
TETRAHEDRON, 2010, 66 (14) :2624-2632
[14]   N-azinylpyridinium N-aminides:: tandem reactions with α-halocarbonyl derivatives and analogs [J].
de la Rosa, R ;
Martínez-Barrasa, V ;
Burgos, C ;
Alvarez-Builla, J .
TETRAHEDRON LETTERS, 2000, 41 (31) :5837-5840
[15]  
de Viedma AG, 1999, J ORG CHEM, V64, P1007
[16]  
Frisch M. J., 2003, Gaussian 03
[17]   INFLUENCE OF POLARIZATION FUNCTIONS ON MOLECULAR-ORBITAL HYDROGENATION ENERGIES [J].
HARIHARA.PC ;
POPLE, JA .
THEORETICA CHIMICA ACTA, 1973, 28 (03) :213-222
[18]   DEVELOPMENT OF THE COLLE-SALVETTI CORRELATION-ENERGY FORMULA INTO A FUNCTIONAL OF THE ELECTRON-DENSITY [J].
LEE, CT ;
YANG, WT ;
PARR, RG .
PHYSICAL REVIEW B, 1988, 37 (02) :785-789
[19]   Pyridinium N-(2′-azinyl)aminides:: Regioselective synthesis of 2-alkylaminoazines [J].
Martínez-Barrasa, V ;
Delgado, F ;
Burgos, C ;
García-Navío, JL ;
Izquierdo, ML ;
Alvarez-Builla, J .
TETRAHEDRON, 2000, 56 (16) :2481-2490
[20]   Universal Features of the Electron Density Distribution in Hydrogen-Bonding Regions: A Comprehensive Study Involving H•••X (X = H, C, N, O, F, S, Cl, π) Interactions [J].
Mata, Ignasi ;
Alkorta, Ibon ;
Molins, Elies ;
Espinosa, Enrique .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (08) :2442-2452