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Quantum‐Chemical Study of Phenylcarbamates with Local Anesthetic Activity
Author(s) -
Remko Milan,
Sekerka Ivan,
van Duijnen Piet Th.
Publication year - 1984
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19843170110
Subject(s) - chemistry , conformational isomerism , intramolecular force , ab initio , protonation , quantum chemical , chemical shift , hydrogen bond , computational chemistry , stereochemistry , ab initio quantum chemistry methods , molecule , ion , organic chemistry
The quantum‐chemical PCILO method has been used to perform a conformational analysis of the 1‐[2‐(2‐methoxyphenylcarbamoyloxy)ethyl]piperidine (B) and its cation (BH⊕) which belong to a group of phenylcarbamates with considerable local anesthetic activity. For B the most stable conformation has a gauche arrangement of the O‐C‐C‐N fragment. For BH ⊕ the most stable conformer is stabilized by an intramolecular hydrogen bond of the N⊕‐H…O=C type. Using the PCILO and “double zeta” ab initio methods the protonation energies were calculated. The gross atomic charges resulting from the “double zeta” ab initio calculations for B and BH ⊕ were compared with the results of the PCILO charge distribution analysis.
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