Substitution effects in N-pyrazole and N-imidazole derivatives along the periodic table

Blanco, Fernando; Alkorta, Ibón; Zborowski, Krzysztof; Elguero, José

doi:10.1007/s11224-007-9237-z

Cited by 14 publications

(9 citation statements)

References 33 publications

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“…6); that is, minima nearer the N1 atom consistently present higher MEP values with excellent quadratic correlation (R 2 = 0.994). The same relationship may be observed for imidazole analogues and has been presented here using the values described in reference [2].…”

Section: Neutral Systems-electrostaticsupporting

confidence: 83%

“…In two recent articles, we have studied the influence of all elements of the second and third rows of the periodic table as substituents of benzene, N-pyrrole, N-pyrazole and N-imidazole [1,2]. Further theoretical studies were devoted to the properties of a selection of pyrazole derivatives; in particular to geometries and methyl stabilization energies [3], GIAO calculations [4] and metallotropic rearrangements [5].…”

Section: Introductionmentioning

confidence: 99%

“…As a continuation of these studies [1,2] and given the importance of the pyridine ring in both chemistry and biology, a comprehensive investigation of its theoretical properties has been undertaken. Moreover, pyridine belongs to the complementary class of p-deficient heterocycles, with benzene being considered to occupy a reference position, being neither p-excessive nor p-deficient [6,7].…”

Section: Introductionmentioning

confidence: 99%

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Substitution effects on neutral and protonated pyridine derivatives along the periodic table

et al. 2008

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A theoretical study of the monosubstitution effects of all atoms of the second and third rows of the periodic table on the a, b and c positions of neutral and protonated pyridine has been carried out by means of B3LYP/6-31 + G(d,p) DFT calculations. The geometric and electronic properties, calculated using the Atoms in Molecules methodology, and the electrostatic potential have been analysed. Concurrently, three separate aromaticity indexes (NICS(0), NICS(1) and HOMA) have been evaluated and compared to the above results. Furthermore, the effect of protonation on these parameters has been investigated. A comparison with analogous results for benzene derivatives has also been carried out.

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Section: Neutral Systems-electrostaticsupporting

confidence: 83%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Substitution effects on neutral and protonated pyridine derivatives along the periodic table

et al. 2008

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“…In the next article, Blanco et al [458] report on the theoretical study of the monosubstitution effects of all the atoms of the second and third row of the periodic table on pyrazole and imidazole, heterocyclic rings of considerable importance in chemistry and biology. Some of the results have been rationalized based on the electronegativity of the substituents and different parameters obtained have been compared with aromaticity indexes.…”

Section: Issuementioning

confidence: 99%

Interplay of thermochemistry and Structural Chemistry, the journal (volume 18, 2007) and the discipline

Ponikvar

Liebman

2008

Struct Chem

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In this study, we relate the contents of the journal Structural Chemistry for the calendar year 2007 and thermochemistry. The year's articles were briefly summarized and a thermochemical comment written to supplement them. Frequently questions were asked and future research was suggested.Keywords Structural Chemistry Á Thermochemistry Á Thermodynamics Á Enthalpy of formation Á Enthalpy of phase change Á Enthalpy of reaction As practiced disciplines, structural chemistry and thermochemistry are very often unrelated. In this study, these disciplines are linked as relations are explicitly made using the contents of the journal Structural Chemistry (Vol. 18) for the calendar year 2007 as a scaffold for our analysis, for our selected articles in the discipline of structural chemistry. These studies have been reviewed by us, where we give them a thermochemical flavor. While this commentary is most generally written in terms of brief summaries of literature papers involving enthalpies of formation and/or reaction, not uncommonly we raise questions and even suggest possible future research. We are not, however, going to give a thermochemical slant on book reviews, honorary dedications, and obituaries although these works will be cited in our text.As such, this article is a sequel to our earlier related reviews of Structural Chemistry for the calendar years 2000 through 2004 [1-5]. Reviews for 2005 and 2006 are currently being prepared. Issue 1In the first article in the first issue of Structural Chemistry for 2007, Hargittai [6] asserted that while research is currently usually carried out in big groups, the most important ideas, observations and discoveries still belong to individuals who have to bring down dogmas or open entirely new areas in science. This may bring solace to the thermochemical community in which research groups are generally small, and the number of new practitioners sadly few.In the past decade, the crystal engineering of multidimensional arrays and networks containing metal ions has achieved considerable progress because of the increased interest in the potential utility of these compounds as zeolite-like materials [7-11], catalysts [12], or magnetic materials [13][14][15]. The thermochemistry of these species is complicated by their inherent complexity: however, estimation approaches of their key thermochemical quantities are increasingly reliable [16]. In the second article of this issue, by Wang et al. [17], the versatility of malonate dianion as a ligand for the construction of extended networks with different topologies dependent on the coordination geometry of the metal ion was discussed. The synthesis and structure of a novel malonate-bridged copper(II) compound in which copper(II) ions have two different coordination environments in a novel three-dimensional (3D) network was described. Metal malonates have been studied from a

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“…Thus, several synthetic methods are now available, and the subsequent preparation of derivatives has been disclosed [10][11][12][13][14][15][16]. The effects of hetero-atom substituents from the second and third row of the periodic table at the nitrogen atom of imidazole have been studied by theoretical methods [17]. However, no experimental details of the molecular geometry of 1-hydroxyimidazole or its salts have yet been reported.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structures of 1-Hydroxyimidazole and Its Salts

Laus

Kahlenberg

2012

Crystals

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Abstract:The crystal structures of 1-hydroxyimidazole and four protic salts (chloride, bromide, sulfate, nitrate) thereof were determined. The molecular geometries (bond lengths and angles) of the free base and the salts were compared. Hydrogen bonding patterns were studied, and OH … N, OH … Cl, OH … Br, OH … O, NH … Cl, NH … Br, and NH … O interactions were identified. Hirshfeld surface analysis gave quantitative insight into these interactions.

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Substitution effects in N-pyrazole and N-imidazole derivatives along the periodic table

Cited by 14 publications

References 33 publications

Substitution effects on neutral and protonated pyridine derivatives along the periodic table

Substitution effects on neutral and protonated pyridine derivatives along the periodic table

Interplay of thermochemistry and Structural Chemistry, the journal (volume 18, 2007) and the discipline

Crystal Structures of 1-Hydroxyimidazole and Its Salts

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