Effects of neutral and charged substituents on the infrared carbonyl stretching frequencies in phenyl and alkyl benzoates in DMSO was written by Nummert, Vilve;Piirsalu, Mare;Vahur, Signe;Toom, Lauri;Leito, Ivo;Koppel, Ilmar A.. And the article was included in Journal of Physical Organic Chemistry in 2017.Electric Literature of C8H7ClO2 This article mentions the following:
The carbonyl IR stretching frequencies for 57 meta-, para- and ortho-substituted Ph benzoates, C6H5CO2C6H4-X and alkylbenzoates, C6H5CO2R, containing besides neutral substituents the charged substituents in phenoxy and alkoxy part in DMSO (DMSO) have been recorded. The carbonyl stretching frequencies, νCO, for meta- and para-substituted Ph esters of benzoic acids in the case of neutral substituents were found to correlate well with the substituent constants, σ°. The νCO values for ortho derivatives correlated with the inductive substituent constants, σI, only. The values of constants for charged substituents, σ°±, calculated on the basis of the νCO and the 13C NMR chem. shifts, δCO, in DMSO agree well with the σ°± values for the corresponding ion pairs reported by Hoefnagel and Wepster and those determined from the log k values of the alk. hydrolysis in 4.4 M NaCl solution at 50 °C. Thus, the values of substituent constants for ion pairs of charged substituents estimated on the basis of aqueous data could be successfully used in non-aqueous solution (DMSO) simultaneously with neutral substituents in case the charged substituents were not completely ionized and are in ion pair form. Copyright © 2016 John Wiley & Sons, Ltd. In the experiment, the researchers used many compounds, for example, Chloromethyl benzoate (cas: 5335-05-7Electric Literature of C8H7ClO2).
Chloromethyl benzoate (cas: 5335-05-7) belongs to organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. Organochlorine compounds are lipophylic, meaning they are more soluble in fat than in water. This gives them a high tenancy to accumulate in the food chain (biomagnification).Electric Literature of C8H7ClO2
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics