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Conformational preference of substituted naphthalenes. 2 —proton–proton coupling constants of hydroxy derivatives of naphthalene
Author(s) -
Salman Salman R.
Publication year - 1984
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270220608
Subject(s) - cndo/2 , naphthalene , proton , conformational isomerism , chemistry , coupling constant , ring (chemistry) , computational chemistry , molecular orbital , coupling (piping) , molecule , materials science , organic chemistry , physics , nuclear physics , particle physics , metallurgy
Long‐range proton–proton coupling constants between the hydroxy proton and ring protons were employed to deduce the conformational preferences of 1‐ and 2‐hydroxynaphthalene. 2,6‐Dibromo‐1,5‐dihydroxy‐naphthalene, 2‐acetyl‐1‐hydroxynaphthalene, 1,6‐dibromo‐2‐hydroxynaphthalene and 2‐hydroxy‐1‐naphthaldehyde were used as model compounds. Molecular orbital calculations at the CNDO/2 and INDO level were used to calculate the energy and the long‐range proton–proton coupling of different conformers of 1‐ and 2‐hydroxynaphthalene.