Cyclic meso-ionic compounds. Part VI. Synthesis, spectroscopic properties, and dipole moments of the isosydnones

MCCARTHY, ALLAN R.; Ollis, W. D.; Barnes, A. N. M.; Sutton, L. E.; Ainsworth, C.

doi:10.1039/j29690001185

Cited by 8 publications

(2 citation statements)

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“…The high dipole moments measured for mesoionic compounds 23 support the charge separation shown by these representations. Cheung et al 24 have proposed that the bonding in these heterocyclic compounds is best viewed as two separate conjugated systems: one bearing a negative charge comprising the S atom, and the C and N atoms at the 3 and 2 ring positions, respectively, and the other bearing a positive charge comprising the N, C, and N atoms at the 1,5, and 4 positions, respectively.…”

Section: Resultssupporting

confidence: 57%

Gold(I) coordination compounds with mesoionic thiolate ligands and the crystal and molecular structure of bis(1,4,5-trimethyl-1,2,4-triazolium-3-thiolate)gold(I) tetrafluoroborate

Deaton¹,

Luss²

1999

J. Chem. Soc., Dalton Trans.

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Section: Resultssupporting

confidence: 57%

Gold(I) coordination compounds with mesoionic thiolate ligands and the crystal and molecular structure of bis(1,4,5-trimethyl-1,2,4-triazolium-3-thiolate)gold(I) tetrafluoroborate

Deaton¹,

Luss²

1999

J. Chem. Soc., Dalton Trans.

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“…The difference of 2.5 eV for the S-2p electrons in (I) and (2) represents, by a similar calculation, a charge difference of 0.49 charge unit. These results confirm Katritzky's view that a betaine structure predominates in the ground state of mesoionic 1,3,4thiadiazolethiones and similar compounds, with charge distribution as shown in the formulations ( I ) , ( 2 ) , and (6).…”

Section: Nomenclature For Intramolecular Exchange Processesmentioning

confidence: 67%

X‐Ray Photoelectron Spectroscopy of Mesoionic Compounds

Patsch

Thieme

1971

Angew. Chem. Int. Ed. Engl.

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Computational Screening of New Orthogonal Metal‐Free Dipolar Cycloadditions of Mesomeric Betaines

Concepción

Авалос

Cintas

et al. 2018

Chemistry A European J

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Computational strategies have gained increasing impact in the de novo design of large molecular sets targeted to a desired application. Herein, DFT-assisted theoretical analyses of cycloadditions, involving mesoionic dipoles and strained cycloalkynes, unveil a series of unexplored mesomeric betaines as vastly superior candidates for orthogonal applications. Thus, isosydnones; thiosydnones; and a six-membered homolog, 6-oxo-1,3-oxazinium-4-olate, exhibit enhanced reactivity with respect to sydnone, which is the archetypal mesoionic ring employed so far in orthogonal chemistry. These compounds were found by assessing energy barriers and transition structures, which are largely governed by electron fluxes from dipolarophile to dipole and noncovalent interactions. Charge-transfer analysis also accounts for previous experimental and theoretical results gathered in the literature, and provides a rationale for further substitution variations. The above naked dipoles release only CO as a byproduct through retro-Diels-Alder of the resulting cycloadducts. These results should invite practitioners to look at such underestimated dipoles and could also help to minimize the number of experiments.

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Cyclic meso-ionic compounds. Part VI. Synthesis, spectroscopic properties, and dipole moments of the isosydnones

Cited by 8 publications

References 0 publications

Gold(I) coordination compounds with mesoionic thiolate ligands and the crystal and molecular structure of bis(1,4,5-trimethyl-1,2,4-triazolium-3-thiolate)gold(I) tetrafluoroborate

Gold(I) coordination compounds with mesoionic thiolate ligands and the crystal and molecular structure of bis(1,4,5-trimethyl-1,2,4-triazolium-3-thiolate)gold(I) tetrafluoroborate

X‐Ray Photoelectron Spectroscopy of Mesoionic Compounds

Computational Screening of New Orthogonal Metal‐Free Dipolar Cycloadditions of Mesomeric Betaines

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