2001
DOI: 10.1107/s1600536801001076
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1,4-Diallylquinoxaline-2,3(1H,4H)-dione

Abstract: The structure of the title compound, C14H14N2O2, has been established. The plane formed by the atoms of the quinoxaline is almost perpendicular to the two allyl groups.

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Cited by 7 publications
(8 citation statements)
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References 4 publications
(1 reference statement)
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“…The quinoxaline ring is planar, which can be attributed to a wide range of electron delocalization. Bond lengths and angles are in accordance with the corresponding reported values in 1,4-dihydroquinoxaline -2,3-dione core (Oxtoby et al, 2005) and other similar N-alkyl quinoxalines (Akkurt et al, 2004;Mustaphi et al, 2001). The existence of (I) in the dione form is evident from C1-O2 [1.226 (3) Å] bond, being smaller than a pure single bond, which confirms the double bond character (Allen et al, 1987 typical for the corresponding single and double bonds, suggesting some degree of delocalization.…”
Section: Data Collectionsupporting
confidence: 89%
See 1 more Smart Citation
“…The quinoxaline ring is planar, which can be attributed to a wide range of electron delocalization. Bond lengths and angles are in accordance with the corresponding reported values in 1,4-dihydroquinoxaline -2,3-dione core (Oxtoby et al, 2005) and other similar N-alkyl quinoxalines (Akkurt et al, 2004;Mustaphi et al, 2001). The existence of (I) in the dione form is evident from C1-O2 [1.226 (3) Å] bond, being smaller than a pure single bond, which confirms the double bond character (Allen et al, 1987 typical for the corresponding single and double bonds, suggesting some degree of delocalization.…”
Section: Data Collectionsupporting
confidence: 89%
“…For general background, see: Zarranz et al (2004); Chowdhury et al (2004); Monge et al (1995); Fuchs et al (2001); Dance (1996); Bernstein et al (1995). For related literature, see: Elina & Tsyrul'nikova (1963); Akkurt et al (2004); Mustaphi et al (2001); Oxtoby et al (2005); Ley & Seng (1975); For bondlength data, see: Allen et al (1987);…”
Section: Related Literaturementioning
confidence: 99%
“…1; relevant geometric parameters are summarized in Table 1. The allylic substituent at the imide N atom of the planar phthalimide adopts a synperiplanar conformation; a similar orientation has been reported for 1,4-diallylquinoxaline-2,3(1H,4H)-dione (Mustaphi et al, 2001). In (I), the allyl group is orthogonal to the the phthalimide ring plane.…”
supporting
confidence: 57%
“… Bond lengths of similar structures (comparison). Refcodes and references: GARROG,11 ZOKWOL,12 VIXCUB01,13 WIKSOZ,21 GURGAB,22 HQOXDO,19 HQOXDO01,18 HQOXDO02,17 QERCOF,16 RAVFEA,15 and LIVSEP 23…”
Section: Resultsmentioning
confidence: 99%