A solvatochromic study of N-[4-(9-acridinylamino)-3-methoxyphenyl]methanesulfonamide hydrochloride: an experimental and theoretical approach.
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 (ν‾A) with (i) traditionally used bulk solvent polarity functions (Δf and F(ε, n)) and (ii) empirical scales of solvent polarity (Z, χB and ETN) 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 (π* and α) was used. The ν‾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.
Department of Molecular Biophysics, Faculty of Biology and Environmental Protection, University of Lodz, Pomorska St. 141/143, 90-236 Lodz, Poland. Electronic address: kanowak@op.pl.
Katarzyna
K
Nowak
D000166:Acridines / Q000737:chemistry*; D000465:Algorithms; D002712:Chlorides / Q000737:chemistry; D006860:Hydrogen Bonding; D016014:Linear Models; D008962:Models, Theoretical; D008968:Molecular Conformation; D009930:Organic Chemicals / Q000737:chemistry; D011522:Protons; D012984:Software; D012997:Solvents / Q000737:chemistry*; D013053:Spectrophotometry; D013449:Sulfonamides / Q000737:chemistry*
D000166:Acridines; D002712:Chlorides; D009930:Organic Chemicals; D011522:Protons; D012997:Solvents; D013449:Sulfonamides; C036871:methanesulfonamide
N-[4-(9-acridinylamino)-3-methoxyphenyl]methanesulfonamide; Solute–solvent interactions; Solvent effects; Solvent polarity scales; m-AMSA