Journal of the Chemical Society. Perkin transactions II p. 675 - 680 (1986)
Update date:2022-07-30
Topics:
Kuroda, Yoshihiro
Fujiwara, Yasuhiro
Kuwae, Akio
Matsushita, Kazuhiro
The sign of the one-bond (15)N-(15)N spin-spin coupling constant, 1J(N-N), of a trans-diazene (4-acetyl-aminoazobenzene) has been determined to test the theoretical prediction that 1)(N-N) would be positive in sign when nitrogens have s-hybridized lone pairs and take a trans conformation.The sign was first determined relative to those of (13)C-(15)N spin-spin coupling constants, nJ(C-N), by selective (15)N decoupling experiments and then finally referenced to that of 1J(C-H) in the benzene ring, which undoubtedly bears a positive sign, by selective (15)N and (1)H decoupling experiments.It was found that the sign of 1J(N-N) of the trans-diazene is negative in contrast to the theoretical prediction.This discrepancy is attributed to the large negative contribution from the orbital-dipole term which was not correctly evaluated in previous calculations for the 1J(N-N) coupling of the N=N bond.
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