Solvent and structural effects on the UV absorption spectra of N-(substituted phenyl)-2-cyanoacetamides

被引:5
作者
Matijevic, Borko M. [1 ]
Vastag, Dendi D. [1 ]
Perisic-Janjic, Nada U. [2 ]
Apostolov, Suzana Lj [1 ]
Milcic, Milos K. [3 ]
Zivanovic, Lidija [3 ]
Marinkovic, Aleksandar D. [4 ]
机构
[1] Univ Novi Sad, Fac Sci, Dept Chem Biochem & Environm Protect, Novi Sad 21000, Serbia
[2] Acad Sci & Arts Vojvodina, Novi Sad 21000, Serbia
[3] Univ Belgrade, Fac Chem, Belgrade 11000, Serbia
[4] Univ Belgrade, Fac Technol & Met, Belgrade 11120, Serbia
关键词
N-(substituted phenyl)-2-cyanoacetamides; UV absorption spectra; Solvent effects; Substituent effects; Ab initio MO calculation; CYANOACETAMIDE DERIVATIVES; BIOLOGICAL EVALUATION; SUBSTITUENT; SOLVATOCHROMISM; ENERGY; SCALE; IR;
D O I
10.1016/j.saa.2013.08.040
中图分类号
O433 [光谱学];
学科分类号
0703 ; 070302 ;
摘要
UV absorption spectra of N-(substituted phenyl)-2-cyanoacetamides have been recorded in the range 200-400 nm in the set of selected solvents. The solute-solvent interactions were analyzed on the basis of linear solvation energy relationships (LSER) concept proposed by Kamlet and Taft. The effects of substituents on the absorption spectra were interpreted by correlation of absorption frequencies with Hammett substituent constant, sigma. It was found that substituents significantly change the extent of conjugation. Furthermore, the experimental findings were interpreted with the aid of ab initio B3LYP/6-311G(d,p) method. Electronic energies was calculated by the use of 6-311++G(3df,3pd) methods with standard polarized continuum model (PCM) for inclusion of the solvent effect. (C) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码:568 / 575
页数:8
相关论文
共 50 条
[41]   Unveiling the antitumor potential of novel N-(substituted-phenyl)-8-methoxycoumarin-3-carboxamides as dual inhibitors of VEGFR2 kinase and cytochrome P450 for targeted treatment of hepatocellular carcinoma [J].
Radwan, Eman M. ;
Abo-Elabass, Eman ;
Abd El-Baky, Atef E. ;
Alshwyeh, Hussah Abdullah ;
Almaimani, Riyad A. ;
Almaimani, Ghassan ;
Ibrahim, Ibrahim Abdel Aziz ;
Albogami, Abdulaziz ;
Jaremko, Mariusz ;
Alshawwa, Samar Z. ;
Saied, Essa M. .
FRONTIERS IN CHEMISTRY, 2023, 11
[42]   Synthesis of 4-(4-ethyl-phenyl)-3-(4-methyl-phenyl)-1,2,4-oxadiazol-5 (4H)-one and 4-(4-ethyl-phenyl)-3-(4-methyl-phenyl)-1,2,4-oxadiazole-5(4H)-thione and solvent effects on their infrared spectra in organic solvents [J].
Kara, Yesim S. ;
Unsal, Mustafa ;
Tekin, Nalan ;
Esme, Asli .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2021, 251
[43]   Synthesis, evaluation and molecular modelling studies of some novel 3-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(substituted-phenyl)propanamides as HIV-1 non-nucleoside reverse transcriptase inhibitors [J].
Murugesan, S. ;
Ganguly, Swastika ;
Maga, Giovanni .
JOURNAL OF CHEMICAL SCIENCES, 2010, 122 (02) :169-176
[44]   Molecular structure, vibrational spectra, RDG, biological activities and experimental and theoretical investigation: N-(4-(- 4-(2-(4-Hydroxyphenyl)-4, 5-diphenyl-1H-imidazol-1-yl) phenylsulphonyl) phenyl) acetamide [J].
Geetha, R. ;
Balachandran, V. ;
Thirughanasambantham, N. ;
Suresh, S. ;
Pradhabhan, D. ;
Saravanan, P. ;
Narayana, B. ;
Radheep, D. Mohan .
RESULTS IN CHEMISTRY, 2025, 16
[45]   Solvent effects on the absorption and emission spectra of novel (E)-4-((4-(heptyloxy)phenyl)diazenyl)benzyl (((9H-fluoren-9-yl) methoxy)carbonyl)-D-alaninate (Fmoc-al-az): Determination of dipole moment by experimental and theoretical study [J].
Varma, Tej Y. ;
Agarwal, Devesh S. ;
Sarmah, Amrit ;
Joshi, Lata ;
Sakhuja, Rajeev ;
Pant, Debi D. .
JOURNAL OF MOLECULAR STRUCTURE, 2017, 1129 :248-255
[46]   Effects of Silver Doping on the Geometric and Electronic Structure and Optical Absorption Spectra of the Au25-nAgn(SH)18- (n=1, 2, 4, 6, 8, 10, 12) Bimetallic Nanoclusters [J].
Guidez, Emilie B. ;
Makinen, Ville ;
Hakkinen, Hannu ;
Aikens, Christine M. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2012, 116 (38) :20617-20624
[47]   STUDIES ON THE BENZOXAZINE SERIES .3. PREPARATION AND C-13 NMR STRUCTURAL STUDY OF GAMMA-EFFECTS OF SOME N-SUBSTITUTED 3,4-DIHYDRO-2H-1,3-BENZOXAZINES [J].
NEUVONEN, K ;
PIHLAJA, K .
MAGNETIC RESONANCE IN CHEMISTRY, 1990, 28 (03) :239-245
[48]   Synthetic, infrared, 1H and 13C NMR spectral studies on N-(p-substituted phenyl)-p-substituted benzenesulphonamides, p-X′C6H4SO2NH-(p-XC6H4), where X′ or X = H, CH3, C2H5, F, Cl or Br [J].
Gowda, BT ;
Jayalakshmi, KL ;
Shetty, M .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES, 2004, 59 (4-5) :239-249
[49]   Synthetic, infrared, 1H and 13C NMR spectral studies on N-(2-/3-substituted phenyl)-4-substituted benzenesulphonamides, 4-X′C6H4SO2NH(2-/3-XC6H4)1 where X′ = H, CH3, C2H5, F, Cl or Br, and X = CH3 or Cl [J].
Gowda, BT ;
Shetty, M ;
Jayalakshmi, KL .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES, 2005, 60 (1-2) :106-112
[50]   Synthetic and spectroscopic studies on N-(i,j-disubstituted phenyl)-4-substituted benzenesulphonamides, 4-X′C6H4SO2NH(i,j-X2C6H3), where X′ = H, CH3, C2H5, F, CL or Br; i,j = 2,3; 2,4; 2,5; 2,6 or 3,4; and X = CH3 or Cl [J].
Shetty, M ;
Gowda, BT .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES, 2005, 60 (1-2) :113-120