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Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

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Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide...
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

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Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α...
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Preparation of 1° Amines: Gabriel Synthesis01:28

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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Diazonium Group Substitution: –OH and –H01:19

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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
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Adenine formation without HCN.

Kenneth M Merz1, Eduardo C Aguiar, Joao Bosco P da Silva

  • 1Quantum Theory Project, University of Florida , 2234 New Physics Building, Gainesville, 32611 Florida, United States.

The Journal of Physical Chemistry. A
|May 7, 2014
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Summary
This summary is machine-generated.

Researchers propose a novel gas-phase adenine synthesis pathway not involving hydrogen cyanide (HCN). This new mechanism, utilizing interstellar molecules, is more efficient and energetically favorable than previous models.

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Area of Science:

  • Astrochemistry
  • Theoretical Chemistry
  • Origin of Life Studies

Background:

  • Adenine synthesis has historically been linked to hydrogen cyanide (HCN) pentamerization.
  • Understanding prebiotic molecule formation is crucial for origin of life research.

Purpose of the Study:

  • To propose and investigate a new gas-phase mechanism for adenine synthesis.
  • To explore alternative pathways for adenine formation using observed interstellar molecules.

Main Methods:

  • Employed retrosynthetic analysis to identify potential precursors.
  • Utilized MP2/6-311++G(2d,2p) computational calculations.
  • Calculated Gibbs free energy for minimum and transition state structures.

Main Results:

  • A six-step mechanism for adenine synthesis from C3NH, HNCNH, and H2NCN was proposed.
  • The new mechanism involves fewer steps and is twice as exergonic.
  • The rate-determining transition state is energetically lower than in previously proposed mechanisms.

Conclusions:

  • This study presents a viable, more efficient gas-phase pathway for adenine formation.
  • The proposed mechanism offers a new perspective on prebiotic adenine synthesis in interstellar environments.