Mamta Sharma Directorate of International Cooperation, Defence Research and Development Organisation, Raja ji Marg, New Delhi-110011, India
Sujeet Kumar Mewar Directorate of International Cooperation, Defence Research and Development Organisation, Raja ji Marg, New Delhi-110011, India
Address for correspondence: Mamta Sharma, Directorate of International Cooperation, Defence Research and Development Organisation, Raja ji Marg, New Delhi-110011, India E-mail: reekana@rediffmail.com
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Sharma M, Mewar SK. Interesting nuclear magnetic resonance studies of some N, N-bis(2-methoxyethyl) substituted benzamides. J Forensic Chem Toxicol. 2023;9(2):77–90.
Timeline
Received : May 30, 2023
Accepted : June 30, 2023
Published : December 12, 2023
Abstract
DEET (N, N Diethyl m-toluamide) and DEPA (Diethyl phenyl acetamide) are synthetic compounds and proven potent insecticide and repellent respectively. In the search of effective mosquito repellent, different derivatives of DEPA or substituted benzamides were synthesized and their NMR analysis was carried out at low temperature. Sterically Crowded Bis (2-methoxyethyl) substituted Benzamides possess low rotational barrier and are floppy at room temperature. Alkyl arms attached to nitrogen become magnetically nonequivalent even at low temperature. Di ortho Substitution in benzamides enhanced hindered internal rotation and resulted splitting in methylene proton signals. The effect of substitution in benzene ring, on the splitting of methylene proton NMR is very well explained and the complete NMR data of substituted benzamides is described in this study for reference purpose.
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Cite this article
Sharma M, Mewar SK. Interesting nuclear magnetic resonance studies of some N, N-bis(2-methoxyethyl) substituted benzamides. J Forensic Chem Toxicol. 2023;9(2):77–90.
This license enables reusers to distribute, remix, adapt, and build upon the material in any medium or format for noncommercial purposes only, and only so long as attribution is given to the creator
This license enables reusers to distribute, remix, adapt, and build upon the material in any medium or format for noncommercial purposes only, and only so long as attribution is given to the creator
1H NMR Chemical shifts of N,N-bis (2-methoxyethyl) Substituted Benzamides for entries 1 to 19 in ppm. (for 2H to 6H Protons)
Description: No description available.
1H NMR Chemical shifts of N,N-bis(2-methoxyethyl) Substituted Benzamides for entries 1 to 19 in ppm. (for 8H to 13H Protons)
Description: No description available.
3D Structure of 2-fluoro-N,N-bis (2-methoxyethyl)benzamide (entry-6) showing connectivity of protons in Space
Description: No description available.
H-1H, 2D-NOESY Spectrum of Benzamide entry 6 Showing Connectivity of H8/H9 with H-6.
Description: No description available.
Graph depicting the chemical shift trend in methyl and methylene protons in entries 1 to 19
Description: No description available.
Expanded 1H NMR Spectra of N,N-bis(2-methoxyethyl) substitued benzamides for entries 3,6,8,11,13,14,15, in CDCl3 showing spitting patterns of methylene protons in the chemical shift range 3 to 4 ppm
Description: No description available.
H-1H COSY Spectrum of entry 13 showing three bond Connectivity for adjacent protons of methylene groups in CDCl3
Description: No description available.
13C{1H} NMR Chemical Shifts of N,N-bis(2-methoxyethyl) Substituted Benzamides for Entries 1 to 19 (1C to 7C).
Description: No description available.
Continued 13C{1H} NMR Chemical Shifts of N,N-bis(2-methoxyethyl) for Entries 1 to 19. (8C to 13C)
Description: No description available.
2D 1H-13C{1H}, HSQC NMR spectrum of entry 13 in CDCl3 showing single bond connectivity of Carbons and Protons
Description: No description available.
: 2D 1H-13C{1H}, HMBC NMR Spectrum of Entry 13 in CDCl3 showing long connectivity of Carbon with Proton