Experimental standard molar enthalpies of formation of crystalline 3,5-dimethylpyrazole, 3,5-dimethyl-4-nitrosopyrazole, 1,3,5-trimethyl-4-nitrosopyrazole, and 3,5-dimethyl-1-phenyl-4-nitrosopyrazole

Silva, Manuel A.V. Ribeiro da; Ferreira, Susana; Rodrigues, Ivone A.P.; Silva, Luı́s C.M. da; Acree, William E.; Pandey, Siddharth; Roy, Lindsay E.

doi:10.1006/jcht.2000.0768

Cited by 10 publications

References 20 publications

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The Organic Thermochemistry of Hydroxylamines, Oximes, Hydroxamic Acids and their Derivatives

Slayden

Liebman

2010

Patai's Chemistry of Functional Groups

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Introduction: Scope of the Chapter, Definitions of Key Terms and Sources of Data Hydroxylamines and N ‐Substituted Derivatives O ‐Substituted Hydroxylamine Derivatives (Alkoxylamines) Monooximes Glyoxime and Other Dioximes Quinone Oximes and Nitrosoarenols Oxime Ethers Hydroxamic Acids and their Derivatives

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The Organic Thermochemistry of Hydroxylamines, Oximes, Hydroxamic Acids and their Derivatives

Slayden

Liebman

2010

Patai's Chemistry of Functional Groups

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Thermochemical Insights on Small Nitrogen Heterocyclic Compounds

Freitas

Silva

2019

Patai's Chemistry of Functional Groups

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Along this overview, a comprehensive thermochemical discussion of small nitrogen heterocyclic molecules is presented, based on reliable information obtained by experimental and computational methodologies. Calorimetric data jointly with other data obtained from alternative sources are used to acquire extensive thermochemical information. A brief description is provided on the more common techniques used in the measurement of properties of compounds under analysis, as well as fundaments on methodologies used in computational approaches, to establish alternative strategies to derive data for other species. Data analysis is fundamentally focused on the standard molar enthalpy of formation, an essential thermodynamic parameter to assess the energy associated to chemical reactions or other transformations involving the compounds, also allowing to derive related thermodynamic properties. This study focuses on neutral, π conjugated, nitrogen heterocyclic five‐membered systems with 1–4 heteroatoms, and some substituted derivatives, complemented by a short discussion on other species having one benzenic ring fused to the heterocycle. Considering its role on chemical structure and reactivity properties, the establishment of intermolecular hydrogen bonding deserved special attention. Complementarily, NH bond dissociation enthalpy values along different aza systems are analyzed and used on comparing thermodynamic favorability of corresponding bond disruptions. An enthalpic parameters database for the selected groups of compounds is reportedly commented, gauging about their reliability to be assumed as key values.

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First N‐Functionalization of 4‐Nitroso‐1H‐Pyrazoles Using Monofunctional and Bifunctional Alkylating Agents

et al. 2023

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The direct N‐alkylation reactions of ambident 3,5‐substituted 4‐nitroso‐1H‐pyrazoles are described for the first time. An efficient method of the 4‐nitroso‐1H‐pyrazoles and their sodium alkyl‐, allyl‐ salts regioselective N‐alkylation by benzyl halides, halocarboxylic acids esters, and related bifunctional alkylating agents is established with the use of superbasic conditions or reflux in acetone. A series of new N‐functionalized nitrosopyrazoles and bis(4‐nitrosopyrazole) compounds is successfully obtained with a yield of up to 85 %. Using quantum‐chemical calculations, it is shown that in terms of kinetics and thermodynamics, the N‐alkylation of the considered pyrazoles is a more advantageous process than O‐alkylation.

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Experimental standard molar enthalpies of formation of crystalline 3,5-dimethylpyrazole, 3,5-dimethyl-4-nitrosopyrazole, 1,3,5-trimethyl-4-nitrosopyrazole, and 3,5-dimethyl-1-phenyl-4-nitrosopyrazole

Cited by 10 publications

References 20 publications

The Organic Thermochemistry of Hydroxylamines, Oximes, Hydroxamic Acids and their Derivatives

The Organic Thermochemistry of Hydroxylamines, Oximes, Hydroxamic Acids and their Derivatives

Thermochemical Insights on Small Nitrogen Heterocyclic Compounds

First N‐Functionalization of 4‐Nitroso‐1H‐Pyrazoles Using Monofunctional and Bifunctional Alkylating Agents

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