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Simakov, V. I.; Kurbatov, S. V.; Borbulevych, O.Y.; Antipin, M. Yu.; Olekhnovich, L. P.

doi:10.1023/a:1011333722238

Cited by 11 publications

(7 citation statements)

References 3 publications

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“…Ninhydrin is a powerful electrophile that reacts not only with amines, enamines, ammonia and amino acids, but also with weak nucleophiles such as anilines, alcohols, ureas and even amides . Many studies have corroborated that upon dehydration of ninhydrin the central carbonyl of the resulting indanetrione is the most reactive towards amines.…”

Section: Introductionmentioning

confidence: 99%

Effect of Substituents on the Reactivity of Ninhydrin with Urea

et al. 2018

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Ninhydrin, i. e. the stable hydrate of the reactive species indanetrione, is a well-known compound used for the quantification of ammonia and amino acids. However, substituent effects on the reactivity of ninhydrin with nucleophiles are not described. In this work, the kinetics of the reaction of C4-and C5-substituted ninhydrins with urea was studied and monitored by 13 C-NMR. Surprisingly, the obtained results show that electron donating groups (EDGs) as well as electron withdrawing groups (EWGs) decrease the rate of the reaction. EDGs decrease the electrophilicity of indanetrione, resulting in slower overall kinetics than unsubstituted ninhydrin. The calculated Gibbs free energy differences for the dehydration of unsubstituted and substituted ninhydrins and the subsequent reaction with urea showed that the dehydration of the compounds is more sensitive to electronic effects than the subsequent reaction with urea. Therefore, although EWGs increase the electrophilicity of indanetrione, this is more than counterbalanced by an adverse shift of the hydration equilibrium towards the unreactive hydrate (i. e. ninhydrin), resulting in slower kinetics as well.[a] J. Scheme 1. The mechanism of reaction of ninhydrin with amino acids. R.d.s. = rate-determining step. 1 e = ninhydrin, Table 1 entry e.

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Section: Introductionmentioning

confidence: 99%

Effect of Substituents on the Reactivity of Ninhydrin with Urea

et al. 2018

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“…[424][425] Scheme 123. The condensation of ortho-aminophenols and N-benzylsulfonyl-o-phenylenediamine with ninhydrin.…”

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confidence: 99%

Ninhydrin in synthesis of heterocyclic compounds

Ziarani¹,

Lashgari²,

Azimian³

et al. 2015

Arkivoc

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Ninhydrin has been utilized in many heterocyclic preparations and considered as an important building block in organic synthesis. There is a wide range of reactions that include ninhydrin in the synthesis of heterocyclic compounds. This review highlights the advances in the use of ninhydrin as starting material in the synthesis of various organic compounds and drugs in a fully comprehensive way, from its first isolation in 1910 to the end of 2013. There is also a diversity of multi-component reactions of ninhydrin and we highlight the recent reports in this review.

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“…Model of garnet-clinopyroxene barometer for deep mantle eclogites were developed on the base of the reaction (Simakov, 1995):…”

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confidence: 99%

Types of eclogite paleogeotherms in the upper mantle

International Kimberlite Conference Extended Abstracts: 1995

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Cited by 11 publications

References 3 publications

Effect of Substituents on the Reactivity of Ninhydrin with Urea

Effect of Substituents on the Reactivity of Ninhydrin with Urea

Ninhydrin in synthesis of heterocyclic compounds

Types of eclogite paleogeotherms in the upper mantle

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