A solvatochromic study of N-[4-(9-acridinylamino)-3-methoxyphenyl] methanesulfonamide hydrochloride: An experimental and theoretical approach

作者：Nowak Katarzyna^*

来源：Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy , 2014, 130: 208-213.

DOI：10.1016/j.saa.2014.03.004

• N-[4-(9-acridinylamino)-3-methoxyphenyl]methanesulfonamide m-AMSA
• Solvent effects
• Solvent polarity scales
• Solute-solvent interactions

The effects of a solvent on the position of the long-wavelength electronic absorption band of N-[4-(9-acridinylamino)-3-methoxyphenyl]methanesulfonamide hydrochloride [m-AMSA.HCl], an antitumor drug, were investigated. To assess the nature of molecular interactions of protonated m-AMSA (1) with various organic solvents the solvatochromic shifts of absorption maxima ((v) over bar (A)) with (i) traditionally used bulk solvent polarity functions (Delta f and F(epsilon,n)) and (ii) empirical scales of solvent polarity (Z,chi(B) and E-T(N)) were analyzed. Additionally, in order to investigate the influence of non-specific and specific solute-solvent interactions on absorption band shifts in protic solvents the multicomponent linear regression with two Kamlet-Taft's solvatochromic parameters (pi* and alpha) was used. The (v) over bar (A) in solvents were also obtained using theoretical calculations with the AM1-SM5.4 method and compared with experimental values. Finally, all the results show that in aprotic solvents there are general dipolarity/polarizability effects, while in protic solvents specific interactions connected with the formation of hydrogen bonds are additionally observed.

• 出版日期2014-9-15