Brønsted acid-promoted synthesis of common heterocycles and related bio-active and functional molecules

Ponra, Sudipta; Majumdar, K. C.

doi:10.1039/c5ra27069c

Cited by 43 publications

(25 citation statements)

References 755 publications

(179 reference statements)

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“…Although QM8 and QM9 are of unprecedented size compared to previous, common benchmark sets in quantum chemistry of several hundred to thousands of molecules, they still contain only small molecules with restricted elemental diversity (H, C, N, O and F) and with simple bonding patterns [67]. They lack larger, more complex molecules with, e.g., extended heteroaromatic backbones and attached functional groups, as commonly targeted in organic synthesis [6,38] and applied in (opto-)electronic [24,32,33,73] or pharmaceutical research [38,53,69]. We have based the spectroscopic dataset presented in this article on a diverse collection of 64,725 organic crystals that were extracted from the Cambridge Structural Database (CSD) [2] by Schober et al [47,48].…”

Section: Background and Summarymentioning

confidence: 99%

Atomic structures and orbital energies of 61,489 crystal-forming organic molecules

et al. 2020

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Data science and machine learning in materials science require large datasets of technologically relevant molecules or materials. Currently, publicly available molecular datasets with realistic molecular geometries and spectral properties are rare. We here supply a diverse benchmark spectroscopy dataset of 61,489 molecules extracted from organic crystals in the Cambridge Structural Database (CSD), denoted OE62. Molecular equilibrium geometries are reported at the Perdew-Burke-Ernzerhof (PBE) level of density functional theory (DFT) including van der Waals corrections for all 62k molecules. For these geometries, OE62 supplies total energies and orbital eigenvalues at the PBE and the PBE hybrid (PBE0) functional level of DFT for all 62k molecules in vacuum as well as at the PBE0 level for a subset of 30,876 molecules in (implicit) water. For 5,239 molecules in vacuum, the dataset provides quasiparticle energies computed with many-body perturbation theory in the G0W0 approximation with a PBE0 starting point (denoted GW5000 in analogy to the GW100 benchmark set (M. van Setten et al. J. Chem. Theory Comput. 12, 5076 (2016))).

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Section: Background and Summarymentioning

confidence: 99%

Atomic structures and orbital energies of 61,489 crystal-forming organic molecules

et al. 2020

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“…Superacids are important reagents in chemistry due to their applications as catalysts in a great variety of transformations in the chemical industry [5][6][7] and synthesis of organic compounds. [8][9][10][11][12][13] Therefore, in past decades much research interest has been devoted to the design, synthesis and assessment of highly acidic materials. This holds, in particular, for neutral organic superacids, since they possess a number of distinct advantages over their mineral (inorganic) counterparts in solution, being reactive in mild chemical environments.…”

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confidence: 99%

“…Inorganic carborane and dodecaborane acids are another types of Brønsted acids and have received many interests due to their high intrinsic acidity. [30][31][32][33][34] The reported ΔG acid values for CB 11 H 12 H and B 12 H 12 H 2 are 267.5 and 266.5, respectively. [35,36] By introducing EWGs such as F, Cl, CF 3 , and CN, their acidity increases to record values as evidenced with ΔG acid of CB 11 F 12 H as low as 212.8 kcal mol −1 .…”

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confidence: 99%

Superacidity of P(OH)₃ and SO(OH)₂ derivatives of cyclopentadiene and vinylcyclopentadiene in the gas phase: A computational DFT analysis

Valadbeigi

Vianello²

2018

Int J of Quantum Chemistry

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Strong Brønsted acids were designed using a simple strategy of replacing double‐bonded oxygen atoms in mineral acids H3PO4 and H2SO4 with cyclopentadiene and vinylcyclopentadiene moieties, followed by a substitution with strong electron‐withdrawing cyano groups. Their intrinsic gas‐phase acidity was assessed by the B3LYP density functional theory calculations employing the 6‐311++G(d,p) basis set, and many highly potent superacids were identified. The pronounced acidity of these conjugates is due to two predominant factors, namely, (i) an increase in the aromaticity of the five‐membered ring on deprotonation, as evaluated through the NICS parameters, and (ii) an extension of the conjugated π‐network enabled by the cyano groups that efficiently distribute an excess negative charge over a large number of atoms in conjugate bases. The SO(OH)2 derivatives are generally more acidic than the corresponding P(OH)3 counterparts so that the ΔHacid values for the SO(OH)2 and P(OH)3 derivatives with CN substituents evaluated here are 260‐266 and 263‐272 kcal mol−1, respectively. Given the growing interest in highly acidic molecules together with related acidic catalysts and metal complexing agents, the results presented here should direct the attention toward utilizing proposed systems as improved organic materials, and their synthesis is highly recommended.

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“…The two-pot route is widely used for various synthesis of epoxy chalcone derivatives namely naphthofurans [73], 2-arylbenzo-furan [25], hydroxy ketone [74][75][76], hydrazinopyrimidine [77], pyridazine esters [24], azaisoflavones [78], bis-hydrazinecarboximidamide [79], difluoroboron ketoiminate […”

Section: Two-pot Routementioning

confidence: 99%

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

Farooq

Ngaini

2020

Chemistry Africa

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Epoxy chalcone is a heterocyclic molecule and an important precursor for the synthesis of biologically active compounds. This mini-review is elucidating the synthetic strategies of chalcone epoxide via one pot and two pot routes including nature of reactants, nature of catalyst and variety of catalyst to improve yield of desired product, biological applications and advantages and drawbacks of these synthetic strategies. One pot route has wide variety of reactants and efficient one is the condensation of aldehyde and ketone. However, two pot route is consisted of chalcone synthesis preceding to epoxy chalcone. The synthetic routes for the preparation of epoxy chalcone and the usage as a precursor for the synthesis of various organic molecules with biological application is comprehensively discussed. This review is outstanding in organic chemistry and pharmaceutical industries to produce new molecules with various applications. Graphic AbstractO O

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Brønsted acid-promoted synthesis of common heterocycles and related bio-active and functional molecules

Cited by 43 publications

References 755 publications

Atomic structures and orbital energies of 61,489 crystal-forming organic molecules

Atomic structures and orbital energies of 61,489 crystal-forming organic molecules

Superacidity of P(OH)₃ and SO(OH)₂ derivatives of cyclopentadiene and vinylcyclopentadiene in the gas phase: A computational DFT analysis

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

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Brønsted acid-promoted synthesis of common heterocycles and related bio-active and functional molecules

Cited by 43 publications

References 755 publications

Atomic structures and orbital energies of 61,489 crystal-forming organic molecules

Atomic structures and orbital energies of 61,489 crystal-forming organic molecules

Superacidity of P(OH)3 and SO(OH)2 derivatives of cyclopentadiene and vinylcyclopentadiene in the gas phase: A computational DFT analysis

One Pot and Two Pot Synthetic Strategies and Biological Applications of Epoxy-Chalcones

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Superacidity of P(OH)₃ and SO(OH)₂ derivatives of cyclopentadiene and vinylcyclopentadiene in the gas phase: A computational DFT analysis