Structural assignment of Diels-Alder adducts: an experimental and theoretical approach.
A detailed NMR analysis with total assignment of (1)H and (13)C NMR data for the endo and the exo adducts, obtained by Diels-Alder reaction between 2-cyclohexenone and cyclopentadiene, is described. The unequivocal assignment of the endo and exo structures was performed by (1)H and (13)C NMR. These assignments were supported by theoretical chemical shift calculations at GIAO/HF level using 6-311 + g(2d, p) from optimized structures at the B3LYP/6-31g(d) level.
Gomes Constantino
Mauricio
M
Departamento de Química da Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida Bandeirantes, 3900, 14040-901 Ribeirão Preto, SP, Brazil. mgconsta@usp.br
da Silva Filho
Luiz Carlos
LC
Neto
Alvaro Cunha
AC
Gomes Heleno
Vladimir Constantino
VC
da Silva
Gil Valdo José
GV
Callegari Lopes
João Luis
JL
D003512:Cyclohexanones / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure
D003512:Cyclohexanones; D003517:Cyclopentanes; C028215:2-cyclohexen-1-one; C004709:1,3-cyclopentadiene