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Nuclear magnetic resonance of 1,4-benzodiazepines. II Stereochemistry of 1,3-dihydro-2H-1,4-benzodiazepin-2-ones by lanthanide shift reagents

✍ Scribed by G. Romeo; M. C. Aversa; P. Giannetto; M. G. Vigorita; P. Ficarra

Publisher
John Wiley and Sons
Year
1979
Tongue
English
Weight
465 KB
Volume
12
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The sterochemistry of some 1,3‐dihydro‐2__H__‐1,4‐benxodiazepin‐2‐ones, employed as psychotherapeutic agents, is deduced by proton magnetic resonance using the paramagnetic shift reagent Eu(fod)~3~. the lanthanide induced shifts are computer simulated on the basis of the geometric parameters of the protons in different model structures, having intermediate conformations between a cycloheptadiene‐ and a cyclohepatatriene‐like system. N‐Desmethyldiazepam shows a conformational equilibrium between two pseudoboat forms, while the 1‐alkyl substituted derivatives exist, at room temperature, in olny one boat cycloheptatriene‐like conformation.

📜 SIMILAR VOLUMES

Nuclear magnetic resonance of psychother
Nuclear magnetic resonance of psychotherapeutic agents. IV—conformational analysis of 2,3-dihydro-1H-1,4-benzodiazepines
✍ G. Romeo; M. C. Aversa; P. Giannetto; P. Ficarra; M. G. Vigorita 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 English ⚖ 481 KB

## Abstract The lanthanide shift reagent (LSR)/^1^H NMR study of some 7‐chloro‐5‐phenyl‐2,3‐dihydro‐1 __H__‐1, 4‐benzodiazepines shows that these compounds exist in CDCI~3~ solution as two pseudo‐boat conformers, rapidly interconverting at room temperature. Computer simulated lanthanide induced shi