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Title: Distal effect on mass spectral fragmentations of glycolamide esters of 6-methoxy- 2-naphthylacetic acid (6-MNA) and the crystal structure of N,Nʹ -dimethylglycolamide ester of 6-MNA
Authors: Sharma, Pritam Dev
Wadhwa, Lalit Kumar
Chandiran, Senthil Kumar
Singh, Tejvir
Venugopalan, Paloth
Issue Date: Aug-2004
Publisher: NISCAIR-CSIR, India
IPC Code: Int.Cl.7 C 07 C 61/13
Abstract: The spatial proximity allows facile glycolamide (HOCH2CONR1R2) loss from 6-methoxy-2-naphthylacetic ac id (6-MNA) glycolamide esters in their mass spectra. The process occurs through a hydrogen rearrangement followed by a chargeinitiated C-O bond cleavage to give 6-methoxy-2-naphthyl ketene rad ical cation (m/z 198) . However, this fragment ion is completely absent in the mass spectra or various alkyl ester of 6-M N A indicating that in spite or structure similarity between these two types of derivatives, the fragmentation pattern of glycolamide esters is influenced remotely by amide functionality. X-ray studies of N, N - dimethyl derivative indicate that probably, the specific conformation adopted by the molecule has decisive role to play in the observed fragmentation pattern.
Page(s): 1758-1764
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.43B(08) [August 2004]

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