Stoichiometry of formation of Ruhemann's purple in the ninhydrin reaction

Friedman, Mendel; Williams, L. David

doi:10.1016/0045-2068(74)90017-0

Cited by 67 publications

(38 citation statements)

References 40 publications

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“…For imines obtained from reaction of amino acids with ninhydrin, a mechanism of the Strecker degradation was proposed, which includes the anion formed by deprotonation of the carboxyl group as the key intermediate [ 28 – 29 ]. Indeed during geometry optimization we found that the decarboxylation of the anion formed from glycine and ninhydrin occurs without significant energy barrier.…”

Section: Resultsmentioning

confidence: 99%

Strecker degradation of amino acids promoted by a camphor-derived sulfonamide

Carvalho

Ferreira

Knittel

et al. 2016

Beilstein J. Org. Chem.

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SummaryA camphor-derived sulfonimine with a conjugated carbonyl group, oxoimine 1 (O2SNC10H13O), reacts with amino acids (glycine, L-alanine, L-phenylalanine, L-leucine) to form a compound O2SNC10H13NC10H14NSO2 (2) which was characterized by spectroscopic means (MS and NMR) and supported by DFT calculations. The product, a single diastereoisomer, contains two oxoimine units connected by a –N= bridge, and thus has a structural analogy to the colored product Ruhemann´s purple obtained by the ninhydrin reaction with amino acids. A plausible reaction mechanism that involves zwitterions, a Strecker degradation of an intermediate imine and water-catalyzed tautomerizations was developed by means of DFT calculations on potential transition states.

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Section: Resultsmentioning

confidence: 99%

Strecker degradation of amino acids promoted by a camphor-derived sulfonamide

Carvalho

Ferreira

Knittel

et al. 2016

Beilstein J. Org. Chem.

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“…The mechanism of a-amino acid-ninhydrin reaction in aqueous medium has been reported (McCaldin, 1960;Bhaleker and Engberts, 1978;Friedman and Williams, 1974;Khan, 1989, 1990;Khan and Ali, 1997;Kabir-UdDin, 2000a). The loan pair of electrons of amino nitrogen attack on the carbonyl-carbon of ninhydrin in the primary step to give a Schiff base.…”

Section: Mechanismmentioning

confidence: 94%

“…The kinetics of the reaction in aqueous organic solvents (McCaldin, 1960;Bhaleker and Engberts, 1978;Friedman and Williams, 1974;Khan, 1989, 1990) and in the presence of surfactants (Khan and Ali, 1997;Kabir-Ud-Din et al, 2000a, b) have been studied extensively. The inhibition effect of cationic or anionic micelles on the rate of reaction of ninhydrin with some amino acids has been accounted for the distribution of substrate into both micellar and aqueous pseudo-phase and on the association of the substrate with surfactant (Kabir- UdDin et al, 2000a).…”

Section: Introductionmentioning

confidence: 99%

Hydrotropic Enhancement of Rate of Ninhydrin‐α‐Amino Acid Reaction: A Kinetic Study

Pandey

Upadhyay

2006

Journal of Dispersion Science and Technology

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The kinetics of ninhydrin-a-amino acid (alanine, phenylalanine, and valine) reaction have been studied in the absence and in the presence of a common hydrotrope, sodiumbenzoate. A strong enhancement in the rate of reaction has been observed in the presence of the hydrotrope above its minimal hydrotrope concentration (MHC). The order of reaction in ninhydrin was always found to be unity while that in amino acid decreases from unity to zero at higher [Aminoacid]. A mechanism consistent with kinetic data and involving the formation of a mixed aggregation assemblies between amino acid and hydrotrope has been proposed.

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“…4 The reaction of ninhydrin 1 with amines usually leads to a single product known as Ruhemann's purple 2; as a result, it is used in a variety of analytical techniques. [5][6][7][8][9] This reaction starts with the formation of a Schiff base, which tautomerizes and hydrolyzes to form an aldehyde and Ruhemann's purple 2 by interaction with a second molecule of ninhydrin (Scheme 1). 9 Recent studies showed that dopamine 3 (3,4-dihydroxyphenethylamine) does not form the expected Ruhemann's purple 2 and, when reacting with ninhydrin, produces a mixture of spiro-tetrahydroisoquinoline-type 4 regioisomers by a PictetSpengler condensation (Scheme 2).…”

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confidence: 99%