Electron Ionization (EI) Induced Mass Spectral Analysis of Substituted Phenylacetamides

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Available online at 
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Pelagia Research Library
Der Chemica Sinica, 2017, 8(1):218-222
Pelagia Research Library
218
ISSN : 0976-8505
CODEN (USA): CSHIA5
Electron Ionization (EI) Induced Mass Spectral Analysis of Substituted 
Phenylacetamides
Priyanka Gupta
1
, Sanjay Kumar Srivastava
2
 and Kumaran Ganesan
1
*
1
Synthetic Chemistry Division, Defence Research and Development Establishment (DRDE), Jhansi Road, Gwalior (MP), India
2School of Studies in Chemistry, Jiwaji University, Gwalior (MP), India
ABSTRACT
A variety of substituted Phenylacetamides of piperidine and morpholine as potent mosquito repellents have been synthesized and 
their mass spectral fragmentation pattern under electron impact have been studied. All these amides follow a unique pattern in 
their mass spectra fragmentation and formation of the fragment ions depends on the substitution on both the phenyl ring and 
amines. These fragmentation patterns are useful for unambiguous identification of these amides during their GC MS analysis.
Keywords:
Phenylacetamides, Piperidines, Morpholines, Electron impact, Mass spectra
INTRODUCTION
Amides and their derivatives constitute an important class of organic compounds and exhibit a wide range of 
biological properties such as anti-inflammatory [1], anticonvulsant [2], antifungal [3], insecticidal [4] anti-tumor [5], 
anti-tuberculosis [6] and mosquito repellent activity [7]. In fact, about 25% of known pharmaceuticals contained 
at least one amide bond [8]. Amides like N, N-Diethyl-m-toluamide (DEET) [9], Diethylbenzamide (DEB) [10] 
and N, N-Diethyl-2- phenylacetamide (DEPA) [11] are the most commonly used mosquito repellents all over the 
world. Among them, DEPA has been extensively evaluated as multi-insect repellent in the laboratory and field and 
found effective against different insect vectors such as mosquitoes, simuliidaes, sand flies, ticks, rat flea and blood 
sucking flies [12-14]. It has been granted approval by the Drug Controller of India
for use on humans [15] and is 
now available in market as lotion, cream and in spray formulations. Two DEPA analogues, viz., DM 156 and DM 
34, show promising repellency and low toxicity [16] against Aedes aegypti.
As an extension of our previous work 
on the development of more potent DEPA analogues [17], our present research program involves the synthesis and 
characterization of substituted phenylacetamides followed by their screening as potent mosquito repellents. Mass 
spectral analysis of these amides is an interesting research area. Numerous reports have been published in the literature 
for their spectral analysis. However, to the best of our knowledge, no systematic study could be found on the mass 
spectral analysis of phenylacetamides of piperidine and morpholine and we, herein, describe the electron induced 
mass spectral fragmentation pattern of these amides differing in the nature of substituents both on the phenyl ring of 
the carboxylic acid as well as in the nature of amine counterparts.