Reaction of 1,1-Dinitroethane with its Salts<sup>1</sup>

Belew, J. S.; Grabiel, Charles E.; Clapp, Leallyn B.

doi:10.1021/ja01610a009

Cited by 24 publications

(3 citation statements)

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“…Belew and co-workers (13) found that 1,1-dinitroethane reacted with its nitrogen base salts to give a coupled product of unresolved structure. Analytical data and reactions of the product indicate its structure is either I or II.…”

Section: Addition Reactions a Michael Reactionmentioning

confidence: 99%

Chemistry of the Aliphatic Polynitro Compounds and Their Derivatives

Noble¹,

Borgardt²,

Reed³

1964

Chem. Rev.

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CiHiOCOCHaCOOH70% HNOi CaHiOCOC(NOi)iH n»n 1.4321 11 98 CiHiOCOCH(CHi)COOH 70% HNOi CaHiOCOC(NOa)aCHi 45(0.1); 7i»D 1.4327 17 98 CaHiOCOCH(CaHí)COOH 70% HNOi CaHiOCOC(NOa)aCaHi 50(0.1); n"D 1.4340 17 98 CiH60COCH(t¡-C.Hi)COOH 70% HNOi CaHsOCOC(NOa)aC,Hi 60(0.1); n»D 1.4393 8 Salts op Polynitro Compounds and Halogen Derivatives Nitronate salt Ci NaO,N=CH(NOi) KO,N=CH(NO,) AgO,N=CH(NO,) (0,N),C=N0, "C«HiN +=N C, Na+[C(NO,),CNJ-K+1C(N0,),CN]" Ag + [C

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Section: Addition Reactions a Michael Reactionmentioning

confidence: 99%

Chemistry of the Aliphatic Polynitro Compounds and Their Derivatives

Noble¹,

Borgardt²,

Reed³

1964

Chem. Rev.

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“…The infrared spectrum verified the presence of the gem-dinitro group with absorption at 7.45 and 7.55 µ. 6 The n.m.r. spectrum verified the presence of one ethyl and one phenyl group in the compound.…”

Section: Phenylation Of Dinitroalkanesmentioning

confidence: 77%

Nuclear Magnetic Resonance Determination of Substituent Methyls in Fatty Acids¹

Cason¹,

Lange²

1964

J. Org. Chem.

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“…Interestingly, the central carbon atom of the DNE carbanion should have sp 2 hybridization, and hence, the “free” anion should be planar (except for protons of methyl group, of course) . The structure of the DNE carbanion was investigated previously by IR , and X-ray methods in the cases of its potassium and sodium salts.…”

Section: Introductionmentioning

confidence: 99%

NMR Study of CHN Hydrogen Bond and Proton Transfer in 1,1-Dinitroethane Complex with 2,4,6-Trimethylpyridine

2015

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The intermolecular complex with a CHN hydrogen bond formed by 1,1-dinitroethane (DNE) and 2,4,6-trimethylpyridine (collidine) dissolved in CD2Cl2 was studied experimentally by (1)H NMR spectroscopy at 180-300 K. Equilibrium between the molecular CH···N form and the zwitterionic C(-)/HN(+) form was detected in the slow exchange regime in the NMR time scale. No sign of a direct C(-)···HN(+) bond was observed; the ion pair is likely to be held by Coulomb interactions. Moreover, there are indications that the protonated base is involved in the formation of homoconjugated (NHN)(+) collidine-collidinium hydrogen bonded complexes. The reaction pathway of proton transfer in the DNE-pyiridine complex in a vacuum was studied computationally at the B3LYP/6-31++G(d,p) level of theory. NMR chemical shifts and coupling constants were calculated for a series of snapshots along the proton transfer coordinate. While the central carbon atom has a pyramidal (sp(3)) configuration in DNE, it is flat (sp(2)) in the DNE carbanion. As a result, the most indicative computed NMR parameter reflecting hybridization of a carbon atom appeared to be (1)JCC, which starts to change rapidly as soon as a structure with a quasi-symmetric C··H··N bond is reached. Couplings within the hydrogen bridge, (1)JCH, (1h)JHN, and (2)JCN, can serve as good indicators of the degree of proton transfer.

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Reaction of 1,1-Dinitroethane with its Salts¹

Cited by 24 publications

References 0 publications

Chemistry of the Aliphatic Polynitro Compounds and Their Derivatives

Chemistry of the Aliphatic Polynitro Compounds and Their Derivatives

Nuclear Magnetic Resonance Determination of Substituent Methyls in Fatty Acids¹

NMR Study of CHN Hydrogen Bond and Proton Transfer in 1,1-Dinitroethane Complex with 2,4,6-Trimethylpyridine

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Reaction of 1,1-Dinitroethane with its Salts1

Cited by 24 publications

References 0 publications

Chemistry of the Aliphatic Polynitro Compounds and Their Derivatives

Chemistry of the Aliphatic Polynitro Compounds and Their Derivatives

Nuclear Magnetic Resonance Determination of Substituent Methyls in Fatty Acids1

NMR Study of CHN Hydrogen Bond and Proton Transfer in 1,1-Dinitroethane Complex with 2,4,6-Trimethylpyridine

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Reaction of 1,1-Dinitroethane with its Salts¹

Nuclear Magnetic Resonance Determination of Substituent Methyls in Fatty Acids¹