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Synthesis and structural studies of symmetric and unsymmetric adamantylmethyleneazines
Author(s) -
Sanz Dionisia,
Alejandra Ponce María,
María Claramunt Rosa,
FernándezCastaño Cristina,
FocesFoces Concepción,
Elguero José
Publication year - 1999
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199906)12:6<455::aid-poc146>3.0.co;2-3
Subject(s) - azine , chemistry , ab initio , ketone , crystallography , computational chemistry , solid state , crystal structure , quantum chemical , chemical shift , stereochemistry , molecule , organic chemistry
The synthesis and spectroscopic properties ( 1 H, 13 C and 15 N NMR, in solution and in the solid state) of six new 1‐adamantylmethylene azines are reported. The crystal and molecular structures of 1‐adamantylcarbaldehyde azine and 1‐adamantyl methyl ketone azine, which exist in the solid state in the E , E ‐configuration, were determined by x‐ray analysis. The geometric characteristics of the azine central bridge and the preferred configuration with regard to it ( E , E , E , Z or Z , Z ) were investigated by means of the crystallographic data retrieved from the Cambridge Structural Database and ab initio quantum chemical calculations. Copyright © 1999 John Wiley & Sons, Ltd.