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Conformational analysis of heterocyclic analogues of 5,6,11,12-tetrahydrodibenzo[a,e]cyclooctene: 6,7,14,15-tetrahydrobisbenzimidazo[1,2-a:1′,2′-e][1,5]diazocine and 6,7,13,14-tetrahydrobispyrido[1,2-a:1′,2′-e]diazocinediium dibromide

✍ Scribed by Rosa Ma Claramunt; JoséLuís Lavandera; Dionisia Sanz; José Elguero; María Luisa Jimeno

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
555 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

The IH and I3C NMR spectra of the title compounds have been recorded. While the spectrum of 6,7,14,15-tetrahydrobisbenzimidazo[ 1,2-a: l',2'-e] [ i ,5]diazoeine 3 does not show any dependence with the temperature in the studied range (-65 to +75 "C), that of 6,7,13,14-tetrahydrobispyrido[1,2a: l',2'-e] diazocinediium dibromide 4 shows a clear variation, narrow lines appearing only at + 85 "C. The differences in the dynamic behaviour of these compounds has been analyzed using different semi-empirical calculations (MNIX), AMI, PM3) of the ground and transition states. For comparison purposes, two other compounds belonging to the 6,8,6 series of ring derivatives have also been calculated, 5,6,11,12tetrahydrodibenzo[a,e] cyclooetene 1 and5 ,6,12.13 -tetrahydrobispyrazolo [ 1,2 -a: 1 ',2'-e] [ 1,2,5,6] tetrazoeinediium cation 2.

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