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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
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Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
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Formal Charges02:42

Formal Charges

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In some cases, there are seemingly more than one valid Lewis structures for molecules and polyatomic ions. The concept of formal charges can be used to help predict the most appropriate Lewis structure when more than one reasonable structure exists.
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Complex between Formic Acid and Nitrous Oxide: A Matrix-Isolation and Computational Study.

Luís Duarte1, Iiris Rekola1, Leonid Khriachtchev1

  • 1Department of Chemistry, University of Helsinki , P.O. Box 55, FI-00014 Helsinki, Finland.

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Summary

Researchers investigated formic acid (FA) and nitrous oxide (N2O) complexes, identifying specific structures using spectroscopy and computational methods. The study found that these complexes exhibit enhanced stability compared to FA monomers.

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Area of Science:

  • Physical Chemistry
  • Computational Chemistry
  • Spectroscopy

Background:

  • Formic acid (FA) and nitrous oxide (N2O) are important molecules in atmospheric and chemical processes.
  • Understanding intermolecular interactions is crucial for predicting chemical reactivity and stability.
  • The FA-N2O complex represents a model system for studying hydrogen bonding and non-covalent interactions.

Purpose of the Study:

  • To experimentally and computationally characterize the structures of formic acid-nitrous oxide complexes.
  • To investigate the stability and spectral properties of different FA···N2O isomers.
  • To compare the stability of FA···N2O complexes with that of the formic acid monomer.

Main Methods:

  • Density functional theory (DFT) calculations (M06-2X, wB97XD) and high-level ab initio methods (MP2, CCSD(T)-F12a) were employed.
  • Infrared (IR) spectroscopy in an argon matrix was used for experimental identification of complex structures.
  • Vibrational excitation and thermal annealing techniques were utilized to prepare specific isomers.

Main Results:

  • Eight trans-FA···N2O and nine cis-FA···N2O structures were computationally predicted.
  • Two trans (1t, 3t) and two cis (1c, 3c) structures were experimentally identified via IR spectroscopy.
  • Specific isomers (1t, 1c) with bonded OH groups were observed, while others (3t, 3c) with free OH groups were prepared and studied.
  • Structure 3t was found to be thermally unstable, relaxing to 1t at ~15 K.
  • The cis-FA···N2O complexes (1c, 3c) exhibited significantly longer lifetimes (81.5 min, 18.7 min) than the cis-FA monomer (6.3 min) in an argon matrix at 4.3 K.

Conclusions:

  • The study successfully identified and characterized multiple isomers of the FA···N2O complex.
  • Experimental evidence supports the computational predictions of various complex structures.
  • The FA···N2O complexes, particularly cis isomers, demonstrate enhanced stability compared to the formic acid monomer, attributed to calculated stabilization barriers.