This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Citing Articles Citing Articles via Google Scholar Google Scholar Articles by Chang, S.-K. Articles by Vohra, S. K. Search for Related Content PubMed PubMed Citation Articles by Chang, S.-K. Articles by Vohra, S. K.

Accelerating Effect of Ascorbic Acid on N-Nitrosamine Formation and Nitrosation by Oxyhyponitrite¹

Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, and the Fels Research Institute, Temple University, Philadelphia, Pennsylvania 19140

The reaction of nitrite ion with ascorbic acid and its effect on the rate of nitrosation of secondary amines have been investigated by differential pulse polarography in aqueous acidic solution. Ascorbic acid shows nonuniform behavior: it accelerates the nitrosation of N-methylaniline between pH 1.00 and 1.95, allows the nitrosation of diphenylamine and iminodiacetonitrile, but inhibits the nitrosation of secondary amines, such as dimethylamine, diethylamine, proline, hydroxyproline, N-methylaminoacetonitrile, N-methylaminopropionitrile, and sarcosine. The nitrosating agent generated by the reaction between ascorbic acid and nitrite ion appears to be oxyhyponitrite ion (N₂O₃^-2).

¹ This investigation was supported by Grants CA-18618 and 12227 awarded by the National Cancer Institute, HEW.

² Present address: Johnson & Johnson Co., New Brunswick, N. J.

³ Present address: Leeds & Northup Co., North Wales, Pa.

⁴ Present address: Widener College, Chester, Pa.

⁵ To whom requests for reprints should be addressed at Department of Chemistry, Temple University, Philadelphia, Pa. 19122.

Received 4/ 5/79. Accepted 6/25/79.