Synthetic, Infrared, 1Hand 13CNMR 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

2004 ◽  
Vol 59 (4-5) ◽  
pp. 239-249
Author(s):  
B. Thimme Gowda ◽  
K. L. Jayalakshmi ◽  
Mahesha Shetty
Keyword(s):  
Solid State ◽  
General Formula ◽  
Infrared Spectra ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Vibrational Frequencies ◽  
Spectral Studies ◽  
Benzene Rings ◽  
Electron Donating Groups ◽  
C Nmr

Thirty N-(p-substituted phenyl)-p-substituted benzenesulphonamides of the general formula, p-X’C6H4SO2NH(p-XC6H4), where X’ or X = H, CH3, C2H5, F, Cl or Br, are synthesised and their infrared spectra in the solid state and 1H and 13C NMR spectra in solution are measured. The N-H stretching vibrational frequencies, νN−H vary in the range 3334 - 3219 cm−1, while the asymmetric and symmetric SO2 vibrations appear in the ranges 1377 - 1311 cm−1 and 1182 - 1151 cm−1, respectively. The compounds exhibit S-N and C-N stretching vibrational absorptions in the ranges 937 - 898 cm−1 and 1310 - 1180 cm−1, respectively. There are no particular trends in the variation of these frequencies on substitution with either electron withdrawing or electron donating groups. The 1H and 13C chemical shifts of N-(p-substituted phenyl)-p-substituted benzenesulphonamides,are assigned to various protons and carbons of the two benzene rings. Further, incremental shifts of the ring protons and carbons due to -SO2NH(p-XC6H4) groups in the compounds of the formula, C6H5SO2NH(p-XC6H4), and p-X’C6H4SO2- and p-X’C6H4SO2NH- groups in the compounds of the formula, p-X’C6H4SO2NH(C6H5) are computed and used to calculate the 1H and 13C chemical shifts of the parallely substituted compounds of the general formula p-X’C6H4SO2NH(p-XC6H4). The computed values agree well with the observed chemical shifts. The above incremental shifts are found to correlate with the Hammett substituent parameters.

Synthetic, Infrared, 1H and 13C NMR Spectral Studies on N-(2/3/4-Substituted Phenyl)-2,4-Disubstituted Benzenesulphonamides, 2,4-(CH3)2/2-CH3-4-Cl/2,4-Cl2C6H3SO2NH(i-XC6H4) (i-X = H, 2-CH3, 3-CH3, 4-CH3, 2-Cl, 3-Cl, 4-Cl, 4-F, 4-Br)

2006 ◽  
Vol 61 (10-11) ◽  
pp. 600-606
Author(s):  
Savitha M. Basappa ◽  
Basavalinganadoddy Thimme Gowda
Keyword(s):  
Solid State ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Spectral Studies ◽  
1H And 13C Nmr ◽  
Nmr Chemical Shifts ◽  
Benzene Rings ◽  
Stretching Vibrations ◽  
Absorption Frequencies ◽  
C Nmr

Twenty six N-(2/3/4-substituted phenyl)-2,4-disubstituted benzenesulphonamides of the general formulae 2,4-(CH3)2C6H3SO2NH(i-XC6H4), 2-CH3-4-ClC6H3SO2NH(i-XC6H4) and 2,4- Cl2C6H3SO2NH(i-XC6H4), where i-X = H, 2-CH3, 3-CH3, 4-CH3, 2-Cl, 3-Cl, 4-Cl, 4-F or 4-Br, have been prepared, characterized and their infrared spectra in the solid state and 1H and 13C NMR spectra in solution studied. The infrared N-H stretching vibrational frequencies vary in the range 3298 - 3233 cm−1. Asymmetric and symmetric SO stretching vibrations appear in the ranges 1373 - 1311 cm−1 and 1177 - 1140 cm−1, respectively, while C-S, S-N and C-N stretching absorptions vary in the ranges 840 - 812 cm−1, 972 - 908 cm−1 and 1295 - 1209 cm−1, respectively. The various 1H and 13C NMR chemical shifts are assigned to the protons and carbon atoms of the two benzene rings in line with those for similar compounds. The incremental shifts due to the groups in the parent compounds have been computed by comparing the chemical shifts of the protons or carbon atoms in these compounds with those of benzene or aniline, respectively. The computed incremental shifts and other data were used to calculate the 1H and 13C NMR chemical shifts of the substituted compounds in three different ways. The calculated chemical shifts by the three methods compared well with each other and with the observed chemical shifts. It is observed that there are no particular trends in the variation of either the infrared absorption frequencies or the chemical shifts with the nature or site of substitution.

scholarly journals Synthetic, Infrared, 1H and 13C NMR Spectral Studies on N-(2-/3-Substituted Phenyl)-4-Substituted Benzenesulphonamides, 4-X’C6H4SO2NH(2-/3-XC6H4), where X’ = H, CH3, C2H5, F, Cl or Br, and X = CH3 or Cl

2005 ◽  
Vol 60 (1-2) ◽  
pp. 106-112 ◽  
Author(s):  
B. Thimme Gowda ◽  
Mahesha Shetty ◽  
K. L. Jayalakshmi
Keyword(s):  
Solid State ◽  
13C Nmr ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Spectral Studies ◽  
1H And 13C Nmr ◽  
Methyl Group ◽  
Benzene Rings ◽  
Stretching Vibrations ◽  
C Nmr

Twenty three N-(2-/3-substituted phenyl)-4-substituted benzenesulphonamides of the general formula, 4-X’C6H4SO2NH(2-/3-XC6H4), where X’ = H, CH3, C2H5, F, Cl or Br and X = CH3 or Cl have been prepared and characterized, and their infrared spectra in the solid state, 1H and 13C NMR spectra in solution were studied. The N-H stretching vibrations, νN−H, absorb in the range 3285 - 3199 cm−1, while the asymmetric and symmetric SO2 vibrations vary in the ranges 1376 - 1309 cm−1 and 1177 - 1148 cm−1, respectively. The S-N and C-N stretching vibrations absorb in the ranges 945 - 893 cm−1 and 1304 - 1168 cm−1, respectively. The compounds do not exhibit particular trends in the variation of these frequencies on substitution either at ortho or meta positions with either a methyl group or Cl. The observed 1H and 13C chemical shifts of are assigned to protons and carbons of the two benzene rings. Incremental shifts of the ring protons and carbons due to -SO2NH(2-/3-XC6H4) groups in C6H5SO2NH(2-/3-XC6H4), and 4- X’C6H4SO2- and 4-X’C6H4SO2NH- groups in 4-X’C6H4SO2NH(C6H5) are computed and employed to calculate the chemical shifts of the ring protons and carbons in the substituted compounds, 4-X’C6H4SO2NH(2-/3-XC6H4). The computed values agree well with the observed chemical shifts.

Synthetic, Infrared, 1H And 13C NMR Spectral Studies on Potassium Salts of N-Chloroarylsulphonamides

2004 ◽  
Vol 59 (1-2) ◽  
pp. 64-68
Author(s):  
K. Jyothi ◽  
B. Thimme Gowda
Keyword(s):  
Infrared Spectra ◽  
Phenyl Ring ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Spectral Studies ◽  
Empirical Correlations ◽  
Potassium Salts ◽  
1H And 13C Nmr ◽  
Stretching Vibrations ◽  
Electron Donating Groups

Several N-chloroarylsulphonamides of the configuration, 4-X-C6H4SO2(K)NCl・xH2O (where X = H, CH3, C2H5, F, Cl or Br) and i-X, j-YC6H3SO2(K)NCl・xH2O (where i-X, j-Y = 2,3-(CH3)2; 2,4- (CH3)2; 2,5-(CH3)2; 2-CH3,4-Cl; 2-CH3,5-Cl; 3-CH3,4-Cl; 2,4-Cl2 or 3,4-Cl2) are prepared, characterised, and their infrared spectra in the solid state and NMR spectra in solution are measured and correlated. Comparison of the infrared spectra of the potassium salts of N-chloro-arylsulphonamides with the corresponding arylsulphonamides shows that the strong absorptions in the range 947 - 933 cm−1 are due to N-Cl stretching vibrations. The effect of ring substitution on the N-Cl frequencies is non-uniform. The frequencies in the ranges 1404 - 1370 cm−1 and 1149 - 1125 cm−1 are respectively assigned to S=O asymmetric and symmetric vibrations. The effect of substitution in the phenyl ring in terms of electron withdrawing and electron donating groups is non-systematic. Empirical correlations relating the chemical shifts to the structures are considered. The chemical shifts of aromatic protons and carbons in all the N-chloroarylsulphonamides have been calculated by adding substituent contributions to the shift of benzene, as per the principle of substituent addition. Considering the approximation made, the agreement between the calculated and experimental chemical shifts is reasonably good.

Synthetic, Infrared And Nmr (1H And 13C) Spectral Studies Of N-(Substituted Phenyl)-Methanesulphonamides

2004 ◽  
Vol 59 (7-8) ◽  
pp. 491-500 ◽  
Author(s):  
K. L. Jayalakshmi ◽  
B. Thimme Gowda
Keyword(s):  
Solid State ◽  
Infrared Spectra ◽  
Phenyl Ring ◽  
Chemical Shifts ◽  
Aromatic Proton ◽  
Spectral Studies ◽  
Substituted Anilines ◽  
Substituted Benzenes ◽  
Stretching Vibrations ◽  
Electron Donating Groups

Twenty two N-(substituted phenyl)-methanesulphonamides of the general formula, CH3SO2NHR, where R = 4-XC6H4(X = H, CH3, F, Cl, Br or NO2), i-XC6H4(X=CH3, Cl orNO2 and i=2 or 3) and i, j-X2C6H3(i, j-X2 = 2,3-(CH3)2, 2,4-(CH3)2, 2,5-(CH3)2, 2,6-(CH3)2, 3,5-(CH3)2, 2,3-Cl2, 2,4- Cl2, 2,5-Cl2, 2,6-Cl2 or 3,4-Cl2) were prepared, characterized and their infrared spectra in the solid state and the NMR (1H and 13C) spectra in solution studied. The N-H stretching vibrations absorb in the range, 3298 - 3232 cm−1. Asymmetric and symmetric SO2 stretching vibrations appear as strong absorptions in the ranges, 1331 - 1317 cm−1 and 1157 - 1139 cm−1, respectively. The sulphonamides exhibit S-N stretching vibrations in the range, 926 - 833 cm−1. The effect of substitution in the phenyl ring in terms of electron withdrawing and electron donating groups is non-systematic. The 1H and 13C chemical shifts of N-(substituted phenyl)-methanesulphonamides are assigned to various protons and carbons of the compounds. Further, incremental shifts of the ring protons and carbons due to CH3SO2- and CH3SO2NH- groups in the N-(phenyl)-methanesulphonamide are computed and used to calculate the 1H and 13C chemical shifts of various protons and carbons of N-(substituted phenyl)-methanesulphonamides, by adding substituent contributions to the corresponding aromatic proton or carbon chemical shifts of either aniline, substituted anilines, benzene or substituted benzenes, in different ways, as per the principle of substituent addition. The computed values by different procedures agree well with each other and with the experimental chemical shifts. The correlation of these incremental shifts with the Hammett substituent parameters is poor.

Infrared and NMR (1H & 13C) Spectra of Sodium Salts of N-Bromo-Mono and Di-Substituted-Benzenesulphonamides

2003 ◽  
Vol 58 (5-6) ◽  
pp. 351-356 ◽  
Author(s):  
B. Thimme Gowda ◽  
K. M. Usha
Keyword(s):  
Solid State ◽  
Infrared Spectra ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Vibrational Frequencies ◽  
Sodium Salts ◽  
Stretching Vibrations

Fifteen sodium salts of mono and di-substituted N-bromobenzene-sulphonamides of the configuration, 4-X-C6H4SO2NaNBr (where X = H; CH3; C2H5; F; Cl; Br; or NO2) and i-X,j- YC6H3SO2NaNBr (where i-X, j-Y = 2,3-(CH3)2; 2,4-(CH3)2; 2,5-(CH3)2; 2-CH3,4-Cl; 2-CH3,5-Cl; 3-CH3,4-Cl; 2,4-Cl2 or 3,4-Cl2) are prepared and characterised by measuring their infrared spectra in the solid state and NMR spectra in solution. The N-Br vibrational frequencies, νN−Br of N-bromoarylsulphonamides vary in the range, 945 - 925 cm−1, while the N-Cl vibrational frequencies, νN−Cl, are observed in the range 950 - 927 cm−1 for the corresponding N-chloroarylsulphonamides. Asymmetric and symmetric SO2 stretching vibrations appear in the ranges, 1391 - 1352 cm−1 and 1148 - 1131 cm−1 for the monosubstituted N-bromoarylsulphonamides, while for the disubstituted N-bromocompounds they absorb in the ranges 1391 - 1331 cm−1 and 1149 - 1121 cm−1, respectively. The chemical shifts of aromatic protons and carbon-13 in all the N-bromoarylsulphonamides have been calculated by adding substituent contributions to the shift of benzene and compared with the observed values. The agreement between the calculated and experimental chemical shifts for different protons or carbon-13 is quite good.

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

2005 ◽  
Vol 60 (1-2) ◽  
pp. 113-120 ◽  
Author(s):  
Mahesha Shetty ◽  
B. Thimme Gowda
Keyword(s):  
General Formula ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Substituent Effects ◽  
Spectroscopic Studies ◽  
Methyl Group ◽  
Methods Of Calculation ◽  
Benzene Rings ◽  
Stretching Vibrations ◽  
C Nmr

Fifty four N-(i,j-disubstituted phenyl)-4-substituted benzenesulphonamides of the general formula 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, are prepared and characterized and their infrared, 1H and 13C NMR spectra in solution are studied. The N-H stretching vibrations νN−H absorb in the range 3305 - 3205 cm−1, while the asymmetric and symmetric SO2 vibrations vary in the ranges 1377 - 1307 cm−1 and 1184 - 1128 cm−1, respectively. The N-(i,j-disubstituted phenyl)-4-substituted benzenesulphonamides show C-S, S-N and C-N stretching vibrations in the ranges 844 - 800 cm−1, 945 - 891 cm−1 and 1309 - 1170 cm−1, respectively. The compounds do not exhibit particular trends in the variation of these frequencies on substitution either at ortho or meta positions with either a methyl group or Cl. The observed 1H and 13C chemical shifts ofare assigned to protons and carbon atoms of the two benzene rings. Incremental shifts of the ring protons and carbon atoms due to -SO2NH(i,j-X2C6H3) groups in C6H5SO2NH(i,j-X2C6H3) and 4-X’C6H4SO2NH- groups in 4-X’C6H4SO2NH(C6H*) are computed and employed to calculate the chemical shifts of the ring protons and carbon atoms in the substituted compounds 4-X’C6H4SO2NH(i,j-X2C6H3). The different methods of calculation lead to almost the same values in most cases and agree well with the observed chemical shifts, indicating the validity of the principle of additivity of the substituent effects with chemical shifts in these compounds.

scholarly journals Infrared and NMR Spectra of Arylsulphonamides, 4-X-C6H4SO2NH2 and i-X, j-YC6H3SO2NH2 (X=H; CH3; C2H5; F; Cl; Br; I or NO2 and i-X, j-Y=2,3-(CH3)2; 2,4-(CH3)2; 2,5- (CH3)2; 2-CH3, 4-Cl; 2-CH3, 5-Cl; 3-CH3, 4-Cl; 2,4-Cl2 or 3,4-Cl2)

2002 ◽  
Vol 57 (12) ◽  
pp. 967-973 ◽  
Author(s):  
B. Thimme Gowda ◽  
K. Jyothi ◽  
J. D. D’Souza
Keyword(s):  
Solid State ◽  
Chemical Shift ◽  
Infrared Spectra ◽  
Phenyl Ring ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
High Chemical ◽  
Stretching Vibrations ◽  
Electron Donating Groups ◽  
Experimental Chemical Shift

Several arylsulphonamides of the configuration, 4-X-C6H4SO2NH2 (where X= H; CH3; C2H5;F; Cl; Br; I or NO2) and i-X, j-YC6H3SO2NH2 (where i-X, j-Y=2,3-(CH3)2; 2,4-(CH3)2; 2,5-(CH3)2;2-CH3,4-Cl; 2-CH3,5-Cl; 3-CH3,4-Cl; 2,4-Cl2 or 3,4-Cl2) were prepared, and their infrared spectra were measured in the solid state. The NMR spectra were recorded in solution. N-H asymmetric and symmetric stretching vibrations absorb in the ranges, 3390 - 3323 cm-1 and 3279 - 3229 cm-1,respectively. Asymmetric and symmetric SO2 stretching vibrations appear as strong absorption lines in the ranges, 1344 - 1317 cm-1 and 1187 - 1147 cm-1, respectively. Sulphonamides exhibit S-N stretching vibrational absorptions in the range, 924 - 906 cm-1. The effect of substitution inthe phenyl ring in terms of electron withdrawing and electron donating groups could not be generalised, as the effect is non-systematic. The chemical shift is highly dependent on the electron density around the nucleus or associated with the atom to which it is bonded. Hence empiricalcorrelations relating the chemical shifts to the structures have been discussed. The chemical shifts of aromatic protons and carbons in all the arylsulphonamides have been calculated by adding substituent contributions to the shift of benzene, the principle of substituent addition. Considering the approximation made, the agreement between the calculated and experimental chemical shift values is reasonably good. Generally, electron-withdrawing groups shows high chemicalshifts compared to electron-donating groups.

Spectroscopic Studies with N-Chloroarylsulphonamides: IR and 1H, 13C and 23Na Nmr Spectra of Sodium Salts of N-Chloro-Mono- and Di-Substituted-Benzenesulphonamides, 4-X-C6H4SO2NANCl (X = H; CH3; C2H5; F; Cl; Br; I or NO2) and i-X, j-YC6H3SO2NANCl (i-X, j-Y = 2,3-(CH3)2; 2,4-(CH3)2; 2,5-(CH3)2; 2-CH3, 4-Cl; 2-CH3, 5-Cl; 3-CH3, 4-Cl; 2,4-Cl2 or 3,4-Cl2)

2003 ◽  
Vol 58 (1) ◽  
pp. 51-56 ◽  
Author(s):  
◽  
J. D. D’Souza ◽  
B. H. Arun Kumar
Keyword(s):  
Solid State ◽  
Chemical Shift ◽  
Infrared Spectra ◽  
Phenyl Ring ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Spectroscopic Studies ◽  
Sodium Salts ◽  
Experimental Chemical Shift ◽  
23Na Nmr

In an effort to introduce N-chloroarylsulphonamides of different oxydising strengths, sixteen sodium salts of N-chloro-mono- and di-substituted benzenesulphonamides of the configuration, 4- X-C6H4SO2NaNCl (where X = H; CH3; C2H5; F; Cl; Br; I or NO2) and i-X, j-YC6H3SO2NaNCl (where i-X, j-Y = 2,3-(CH3)2; 2,4-(CH3)2; 2,5-(CH3)2; 2-CH3,4-Cl; 2-CH3,5-Cl; 3-CH3,4-Cl; 2,4- Cl2 or 3,4-Cl2) are prepared, characterized through their infrared spectra in the solid state and NMR spectra in solution. The υN-Cl frequencies vary in the range 950 - 927 cm−1. Effects of substitution in the benzene ring in terms of electron donating and electron withdrawing groups have been considered, and conclusions drawn. The chemical shifts of aromatic protons and carbon-13 in all the N-chloroarylsulphonamides have been calculated by adding substituent contributions to the shift of benzene. Considering the approximation employed the agreement between the calculated and experimental chemical shift values for different protons or carbon-13 is quite good. Effects of phenyl ring substitution on chemical shift values of both 1H and 13C are also graphically represented in terms of line diagrams.

scholarly journals IR and NMR Spectral Studies of Some 4-(6-methoxy-2-naphthyl)-5,6-dihydro-6-(Substituted Phenyl)-4H-1,3-Oxazine-2-Amines: Assessment of Substituent

2013 ◽  
Vol 23 ◽  
pp. 109-116
Author(s):  
Ganesamoorthy Thirunarayanan
Keyword(s):  
Nmr Spectra ◽  
Chemical Shifts ◽  
Statistical Analyses ◽  
Spectral Studies ◽  
Ir And Nmr Spectra ◽  
Effect Of Substituents ◽  
H Nmr ◽  
Substituent Constants ◽  
C Nmr

A series containing thirteen title compounds were synthesized and recorded IR and NMR spectra. The infrared νNH, C=N(cm-1)stretches, 1H NMR δNH, 13C NMR δC=N(ppm) chemical shifts of synthesized oxazine amines were assigned and correlated with Hammett substituent constants, F and R parameters. From the results of statistical analyses, the effect of substituents on the above spectral frequencies can be discussed.

scholarly journals Infrared, 1H and 13C NMR Spectra of N,N-Dichloroarylsulphonamides, 4-X-C6H4SO2NCl2 (X = H, CH3, C2H5, F, Cl or Br) and i-X, j-YC6H3SO2NCl2 (i-X, j-Y = 2,3-(CH3)2, 2,4-(CH3)2, 2,5-(CH3)2, 2-CH3, 4-Cl, 2-CH3, 5-Cl, 3-CH3, 4-Cl, 2,4-Cl2 or 3,4-Cl2)

2003 ◽  
Vol 58 (9-10) ◽  
pp. 563-568
Author(s):  
B. Thimme Gowda ◽  
K. Jyothi ◽  
N. Damodara
Keyword(s):  
Infrared Spectra ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Empirical Correlations ◽  
Absorption Bands ◽  
1H And 13C Nmr ◽  
Modes Of Vibration ◽  
Stretching Vibrations ◽  
Electron Donating Groups ◽  
Infrared Absorption Bands

Several mono- and di-substituted N,N-dichloroarylsulphonamides of the configuration, 4-XC6H4SO2NCl2 (where X = H, CH3, C2H5, F, Cl or Br) and i-X, j-YC6H3SO2NCl2 (where i- X, j-Y = 2,3-(CH3)2, 2,4-(CH3)2, 2,5-(CH3)2, 2-CH3,4-Cl, 2-CH3,5-Cl, 3-CH3,4-Cl, 2,4-Cl2 or 3,4-Cl2), respectively, were prepared, characterised and their infrared spectra in the solid state and NMR spectra in solution state were measured and correlated. Comparison of the infrared spectra of the N,N-dichloroarylsulphonamides with the corresponding arylsulphonamides and Nchloroarylsulphonamides revealed that the infrared absorption bands in the ranges, 790 - 735 cm−1 and 595 - 546 cm−1 are due to N-Cl asymmetric and symmetric stretching vibrations, respectively, and that the effect of ring substitution on the N-Cl frequencies is not consistent. The frequencies in the ranges 1384 - 1333 cm−1 and 1181 - 1143 cm−1 are, respectively, assigned to S=O asymmetric and symmetric modes of vibration. The effect of substitution in the phenyl ring in terms of electron withdrawing and electron donating groups is non-systematic. Since the chemical shift depends on the electron density around the nucleus, empirical correlations relating the chemical shifts to the structures have been considered. The chemical shifts of aromatic protons and carbons in all the N,Ndichloroarylsulphonamides have been calculated by adding substituent contributions to the shift of benzene. Considering the approximation made, the agreement between the calculated and experimental chemical shifts is good.

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