Thermodynamic Properties of Three Pyridine Carboxylic Acid Methyl Ester Isomers

Silva, Manuel A.V. Ribeiro da; Freitas, Vera L.S.; Santos, Luı́s M. N. B. F.; Fulem, Michal; Sottomayor, M.J.; Monte, Manuel J.S.; Acree, William E.

doi:10.1021/je060472e

Cited by 13 publications

(3 citation statements)

References 26 publications

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“…Δ f H 0 for the three pyridinecarboxylic acids and their methyl esters derived from experiment have been reported and are shown in Table . The data are somewhat scattered, but the 2-derivatives have Δ f H 0 values slightly but significantly below their 3- and 4-isomers by margins similar to those for the methyl- and acetylpyridines.…”

Section: Carbon Hydrogen and Nitrogenmentioning

confidence: 99%

Group Additivity Values for Estimating the Enthalpy of Formation of Organic Compounds: An Update and Reappraisal. 2. C, H, N, O, S, and Halogens

Holmes

Aubry

2012

J. Phys. Chem. A

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This study extends a previous publication on group additivity values (GAVs) for the elements C, H, and O, to include the elements nitrogen, sulfur, and the halogens. The present state and utility of the Benson additivity schemes for estimating the enthalpy of formation (Δ(f)H(0)) of organic compounds are again described, extending them to include more elements. Old and new GAVs for a wide variety of compounds are provided and are revised where necessary. When new terms are proposed, or old ones are significantly altered, the rationale for so doing is presented. GAV derived ring strain values for benzene and pyridine indicate that the aromatic stabilization of each is essentially the same. As before, the thermochemical consequences of replacing one functional group by another are also shown, thus permitting quick shortcuts to the estimation of new Δ(f)H(0) values.

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Section: Carbon Hydrogen and Nitrogenmentioning

confidence: 99%

Group Additivity Values for Estimating the Enthalpy of Formation of Organic Compounds: An Update and Reappraisal. 2. C, H, N, O, S, and Halogens

Holmes

Aubry

2012

J. Phys. Chem. A

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“…The contemporary term pyridine was created by combining the Greek words pyr, which means "fire", and iodine, which is the ending for aromatic amines. In order to create pyridine, William Ramsay heated acetylene and hydrogen cyanide in an iron tube in 1876 [2] . Since pyridine is a planar, six-member heterocyclic ring with five carbons and one nitrogen atom, the nitrogen atom is located in the first desired place in the naming N-heterocyclic medicines with pyridine or dihydropyridine rings make up around 14% and 4%, respectively, of all approved prescriptions, according to data from the US Food and Drug Administration (FDA).…”

Section: Introductionmentioning

confidence: 99%

Pyridine derivatives as preferable scaffolds for the process of discovering new drugs

Ali

Mohanty

Elumalai

et al. 2023

ACE

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The pyridine ring is present in numerous significant plant compounds. It is used as a therapeutic to boost the solubility and bioavailability of less soluble chemicals since it is a polar and ionizable aromatic molecule. Chemical compounds derived from pyridine are highly sought-after in the pharmaceutical industry. An essential synthesis strategy in the search for novel medications is the fusion of the pyridine nucleus. Due to the compounds’ powerful therapeutic characteristics, medicinal chemists have long been fascinated by the chemistry of pyridine and its derivatives, which inspires them to look for and make novel compounds with biological utility. There are significant ramifications for medical chemistry in the adaptability of pyridine and its derivatives as reactants and starting materials for structural changes. Pesticides and agricultural chemicals that heavily rely on pyridine derivatives include insecticides, fungicides, and herbicides; However, this page focuses on their medical applications. Pyridine derivatives are frequently used in the textile industry to create dyes. We present the most recent findings from 2010 onward, highlighting the growing significance of pyridine scaffolds in medicinal chemistry and the development of new drugs. Even though there are a lot of studies on pyridine derivatives, this chapter only has compounds with a clear pharmacophore.

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“…The systematic study of thermochemical properties of pyridine derivatives, both in the condensed and gaseous phases, is one of the subjects of our research work. For several years we have studied the thermochemical properties of various pyridine compounds in order to establish how the transferability of bond energy contributions applies to these compounds – and, consequently, to correlate their behavior in terms of energetics, structure and reactivity. In addition we have been examining the effect of different substituents on the dissociation enthalpy of the (N−O) bond of the nitrogen N-oxide heterocycles, a study that requires the knowledge of thermochemical data of the correspondent heterocycles not having the (N−O) bond …”

Section: Introductionmentioning

confidence: 99%

Thermochemical Study of Three Hindered Pyridine Derivatives

2008

Self Cite

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The present work reports the values of the gaseous standard (p°) 0.1 MPa) molar enthalpy of formation of three pyridine derivatives substituted with one, two, and three tert-butyl groups, in positions para, orthoortho and ortho-para-ortho to the nitrogen, respectively. The standard molar energies of combustion of each compound, determined by static bomb calorimetry, yielded their standard molar enthalpies of formation in the condensed phase at T ) 298.15 K, which together with the values of the standard molar enthalpies of vaporization or sublimation, measured by Calvet microcalorimetry, allowed the calculation of the standard gas phase molar enthalpy of formation of each compound studied. The enthalpies of combustion for 4-tertbutylpyridine (l), 2,6-di-tert-butylpyridine (l) and 2,4,6-tri-tert-butylpyridine (cr) were found to be, respectively, -(5 370.1 ( 3.4) kJ mol -1 , -(7954.2 ( 4.0) kJ mol -1 , and -(10 542.9 ( 4.9) kJ mol -1 . The molar enthalpies of vaporization were measured as (54.4 ( 1.3) kJ mol -1 for 4-tert-butylpyridine, (56.6 ( 1.2) kJ mol -1 for 2,6-di-tert-butylpyridine, whereas the enthalpy of sublimation of 2,4,6-tri-tert-butylpyridine was found to be (78.3 ( 1.7) kJ mol -1 .

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Thermodynamic Properties of Three Pyridine Carboxylic Acid Methyl Ester Isomers

Cited by 13 publications

References 26 publications

Group Additivity Values for Estimating the Enthalpy of Formation of Organic Compounds: An Update and Reappraisal. 2. C, H, N, O, S, and Halogens

Group Additivity Values for Estimating the Enthalpy of Formation of Organic Compounds: An Update and Reappraisal. 2. C, H, N, O, S, and Halogens

Pyridine derivatives as preferable scaffolds for the process of discovering new drugs

Thermochemical Study of Three Hindered Pyridine Derivatives

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