FT‐IR, FT‐Raman, and computational calculations of 4‐chloro‐2‐(3‐chlorophenyl carbamoyl)phenyl acetate

Abstract

FT-IR and FT-Raman spectra of 4-chloro-2-(3-chlorophenylcarbamoyl) phenyl acetate were studied. Vibrational wavenumbers and corresponding vibrational assignments were examined theoretically using the Gaussian03 set of quantum chemistry codes and the normal modes are assigned by potential energy distribution (PED) calculations. Simultaneous IR and Raman activation of the C O stretching mode shows the charge transfer interaction through a π-conjugated path. Optimized geometrical parameters of the title compound are in agreement with the reported values. Analysis of the phenyl ring modes shows that C-C stretching mode is equally active as strong bands in both IR and Raman, which can be interpreted as the evidence of intramolecular charge transfer via conjugated ring path and is responsible for hyperpolarizability enhancement leading to nonlinear optical activity. The red-shift of the NH-stretching wavenumber in the infrared spectrum from the computed wavenumber indicates the weakening of the NH bond resulting in proton transfer to the neighboring oxygen atom. Copyright

Quantitative Analysis of the Etherification Degree of Phenolic Hydroxyl Groups in Oxyethylated Lignins: Correlation of Selective Aminolysis with FTIR Spectroscopy

“…Accordingly, intensities of signals at 1190 and 1215 cm –1 , related to υ­(CO–O) in phenolic and aliphatic acetates, respectively, change in the same manner as υ­(CO) phen and υ­(CO) aliph . Thus, the intensity ratio I 1190 / I 1215 of acetylated lignins and OEL is assumed as a suitable and powerful indicator to quantify free phenolic OH groups of lignin and lignin derivatives like OEL as it was described for the aliphatic and aromatic IR ester bands of acetylated milled wood and organosolv lignins at 1745 and 1765 cm –1 . , …”

“…Interestingly, the same relations were found for the intensity I 900 and more distinctive for the peak integral A 900 of the IR band at 900 cm –1 (Figure c, d), attributed to υ­(C–C) in phenolic acetates . Linear regression of these two IR parameters with OH phen contents from aminolysis yielded coefficients of determinations R 2 ≥ 0.94 (Table ).…”

Recent advances in linear and nonlinear Raman spectroscopy. Part IV

“…Anyone interested in the exact methodology used is invited to view the abstract of the paper at the Journal website or to download and read the paper in its entirety. The molecules for which vibrational analysis has been carried out through the standard methods of quantum chemistry are: 4‐chloro‐ and 4‐bromophenylboronic acid,276 4‐( N , N ‐dimethylamino)‐ N ‐methyl‐4′‐toluene sulfonate,277 C 7 H 15 CONH 2 ‐ valpromide,278 L ‐arginine nitrate hemihydrate,279 Azure A chloride, 3‐amino‐7‐(dimethylamino) phenothiazin‐5‐ium chloride,280 8‐( n ‐butylaminophenylmethyliden)‐1,2,3,4,5,6,7‐heptathiocane which contains a CS7 ring,281 N ‐acetyl‐ L ‐Asp and N ‐acetyl‐ L ‐Glu in the solid state,282 N ‐acetyl‐ L ‐Asp‐ L ‐Glu in the solid state,283 7‐chloro‐3‐methyl‐2 H ‐1,2,4‐benzothiadiazine 1,1‐dioxide,284 strontium tartrate (C 4 H 4 O 6 Sr),285 flavonoid derivatives baicalein and naringenin,2863‐{[(4‐fluorophenyl)methylene]amino}‐2‐phenylquinazolin‐4(3 H )‐one,287 1‐benzyl‐1 H ‐imidazole,288 hydrated platinum(II), palladium(II) and cis ‐diammineplatinum(II) ions in acidic solution,289 ibuprofen‐cyclodextrin inclusion complexes,290 the anticancer drug combretastatin‐A2,291 the grossular garnet Ca 3 Al 2 Si 3 O 12 ,292 2‐fluoro‐6‐nitrotoluene,293 (CH 3 ) 3 GeBr,294 benzoic acid and 3,5‐dichloro salicylic acid,295 PCCMB 2,5 dimethyl‐1‐phenylpyrazolium‐3‐carboxylate and its isomer the CCMB 1,3‐dimethyl‐2‐phenylpyrazolium‐4 carboxylate,296 the nonpeptide antagonist irbesartan,297 3‐{[(2‐hydroxyphenyl)methylene]amino}‐2‐phenylquinazolin‐4(3 H )‐one,298 4‐chloro‐2‐(4‐bromophenylcarbamoyl)phenyl acetate,299 1,4,5‐triazanaphthalene,300 Martius yellow sodium salt monohydrate,301 1,3‐dibromo‐2,4,5,6‐tetrafluorobenzene and 1,2,3,4,5‐pentafluorobenzene,302 4‐hydroxy‐3[1‐(4‐nitrophenyl)‐3‐oxobutyl]‐2 H ‐1‐benzopyran‐2‐one, acenocoumarol sodium salt,303 N ‐(2′‐furyl)imidazole,304 N ‐hydroxyphthalimide,305 3,3,7,7‐tetrakis(difluoramino)octahydro 1,5‐dinitro‐1,5‐diazocine,306 p ‐bromonitrobenzene,307 4‐chloro‐2‐(3‐chlorophenylcarbamoyl)phenyl acetate,308 alkylamides of thiocyanoacetic acid,309 1,2‐bis(trifluorosilyl)ethane (SiF3CH2CH2SiF3),310 organomolybdenum dithiolene complexes Cp2Mo(dmit),311 methyl trifluoroacetate (CF3C(O)OCH3),312 nitrofurantoin polymorphs,313 methylcyclohexane,314 ethyl‐3‐(3, 4‐dihydroxyphenyl)‐2‐propenoate,315 anilinium sulfate,316 valpromide and some derivatives with antiepileptic activity,…”