Collect. Czech. Chem. Commun. 1991, 56, 2160-2168

1H and 13C NMR spectra of 2,2’-disubstitutedtrans-azobenzenes suitable for preparation of metallized azo dyes

Josef Jirman

Research Institute of Organic Syntheses, 532 18 Pardubice-Rybitví


The 1H and 13C NMR spectra have been measured of six trans-azobenzenes substituted at 2 and 2’ positions with substituents favourable for complex formation with a metal (OH, NH2, NHCOCH3, COOH). From the standpoint of NMR such substituted trans-azobenzenes are present in solution in a rapid equilibrium following from rotation around the bond between C-1 of phenyl group and N atom of azo linkage. The predominant form has the substituent in the syn-position with respect to the free electron pair of the nearer azo nitrogen atom. The equilibrium is affected by dipolar aprotic solvents (such as hexadeuteriodimethyl sulfoxide) by decreasing the presence of the predominant form by 1 to 11%.