Structure of 3-(p-ethoxyphenyl)sydnone (1), C10H10N2O3, and 3-(p-tolyl)sydnone (2), C9H8N2O2

Wang, Y.; Lee, P. L.; Yeh, M. H.

doi:10.1107/s0108270184007435

Cited by 13 publications

(10 citation statements)

References 2 publications

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“…0108-2701/85/121776-04501.50 tances in the sydnone ring are similar in both structures and also similar to those in 3-(p-ethoxyphenyl)-sydnone and 3-(p-tolyl)sydnone [Wang, Lee & Yeh (1984). Acta Cryst.…”

mentioning

confidence: 52%

“…It is obvious that compound (1) has better planarity than compound (2). The bond lengths of the sydnone ring are compared with those from other 3-phenylsydnone derivatives in Table 2 (Wang, Lee & Yeh, 1984;Hope, 1978). N(1)-C(7) and C(7)-C(8) of the last three compounds in Table 2 are significantly shorter than the corresponding bonds in other 3-phenylsydnone derivatives.…”

Section: /mentioning

confidence: 99%

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Structures of 3-(p-benzyloxyphenyl)sydnone (1) and 3-(p-isopropoxyphenyl)sydnone (2)

Ueng¹,

Lee²,

Wang³

et al. 1985

Acta Crystallogr C

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confidence: 52%

Section: /mentioning

confidence: 99%

Structures of 3-(p-benzyloxyphenyl)sydnone (1) and 3-(p-isopropoxyphenyl)sydnone (2)

Ueng¹,

Lee²,

Wang³

et al. 1985

Acta Crystallogr C

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“…This suggests an iminium-type nature of this nitrogen and therefore has an electron withdrawing impact which will deactivate the attached aryl substituents towards all electrophilic reagents [18]. Even though, the calculated bond order of the N-O was 1.22 Å which was close to 1.14 Å of the double bond N=O, the X-ray confirmed its single bond nature [19,20]. Interestingly, the high electron density of C4 in structures XXV and XXVI was later supported by the finding of Greco and O'Reilly who reported a strong acidity of 3-phenylsydnone with pKa However, more recent studies by Fan and his lab-mates gave a better insight into bond length and nature, atomic charges and electron density distribution for thirteen different sydnone compounds.…”

Section: Physicochemical Properties Of Sydnonementioning

confidence: 83%

“…The calculated bond order value of C5-O6 bond in structure XXV and XXVI [18] along with the X-ray structure of 3-(p-bromophenyl) sydnone [19], 3-(p-ethoxyphenyl) sydnone and 3-(p-tolyl)sydnone [20] pointed out a carbonyl-like double bond characters of the C5-O6 bond of the sydnone ring. Moreover, it can be noticed that the exocyclic oxygen O6 is highly negative charged (-0.53) even stronger than the carbonyl oxygen of butyrolactone (-0.38) indicating a very polarizable carbonyl group [18].…”

Section: Physicochemical Properties Of Sydnonementioning

confidence: 99%

Mesoionic Sydnone: A Review in Their Chemical and Biological Properties

Abdualkader

Taher

Yusoff

2017

Int J Pharm Pharm Sci

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Various literature sources have documented sydnones as important molecules with exclusive chemical properties and a wide spectrum of bioactivities. Sydnone can be defined as a five-membered pseudo-aromatic heterocyclic molecule. Classically, 1,2,3-oxadiazole forms the main skeleton of sydnone. The molecule has delocalized balanced positive and negative charges. The five annular atoms share the positive charge and the enolate-like exocyclic oxygen atom bears the negative charge. The hydrogen atom at the position C4 was proved to have acidic and nucleophilic functionalities making the sydnone ring reactive towards electrophilic reagents. These unique chemical features enable sydnones to interact with biomolecules resulting in important therapeutic effects like anticancer, antidiabetic, antimicrobial, antioxidant and anti-inflammatory. Consequently, we aim from the current article to review the available chemical and pharmacological information on sydnone and its derivatives.

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“…1, in which bond lengths are also shown. The geometry of the methoxy-Ssl~l phenyl ring is quite normal (see, for example, Wang, s(3) Lee & Yeh, 1984). The five-membered 1,2-dithiole-c(I) C(2) 3-thione ring in the present molecule is similar to that of c(3) 4-methyl-5-(2-pyrazinyl)-3H-1,2-dithiole-3-thione (1) c(4) (Wei, 1983); the S(2)-S(3) distance is nearly identical c(5) C(6) with that of compound (1) and is within the range of c (7) S-S single bonds found in simple inorganic sulfur c (8) compounds, e.g.…”

Section: Table 1 Atomic Coordinates and Equivalent Isotropicmentioning

confidence: 99%