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Conformation of 7‐chloro‐5‐phenyl‐ d 5 −3( S )‐methyl‐dihydro‐1,4‐benzodiazepin‐2‐one in solution
Author(s) -
Šunjić V.,
Lisini A.,
Sega A.,
Kovač T.,
Kajfež F.,
Ruščić B.
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160429
Subject(s) - chemistry , reagent , substrate (aquarium) , lanthanide , position (finance) , group (periodic table) , stereochemistry , crystallography , organic chemistry , ion , oceanography , finance , economics , geology
7‐Chloro‐5‐phenyl‐ d 5 ‐3( S )‐methyldihydro‐1,4‐benzodiazepin‐2‐one ( 1a ) was synthesized and its conformation in solution determined using a computer assisted LIS‐NMR method. It was found, with Fr(fod)‐ d 27 as a shift reagent, that a lanthanide coordinates to a carbonyl oxygen at a 2.02 Å distance (bond angle 158.07°, torsional angle 39.53°), while the substrate 1a adopts an expected quasi‐boat conformation with a C(3)‐methyl group exposed in a quasi‐equatorial position.