1,1-Diamino-2,2-dinitroethylenes are always zwitterions

Pessia Gilinsky-Sharon; Hugo E. Gottlieb; David E. Rajsfus; Keren Keinan-Adamsky; Vered Marks; Pinchas Aped; Aryeh A. Frimer

doi:10.1002/mrc.3861

1,1-Diamino-2,2-dinitroethylenes are always zwitterions

Pessia Gilinsky-Sharon, Hugo E. Gottlieb, David E. Rajsfus, Keren Keinan-Adamsky, Vered Marks, Pinchas Aped, Aryeh A. Frimer

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

The nitration of tetraiodoethylene (7) yields 1,1-diiodo-2,2- dinitroethylene (8). The latter reacts with alkylamines 9 or alkyldiamines 11 to give the corresponding acyclic 1,1-diamino-2,2-dinitroethylenes 10 or their cyclic analogs 12, respectively. On the basis of liquid and solid-state ¹³C and ¹⁵N NMR data, x-ray analysis and ab initio calculations, we suggest that the title compounds are always zwitterionic and that the C_A-C_N bond is not a true double bond.

Original language	English
Pages (from-to)	672-679
Number of pages	8
Journal	Magnetic Resonance in Chemistry
Volume	50
Issue number	10
DOIs	https://doi.org/10.1002/mrc.3861
State	Published - Oct 2012

Keywords

13C
15N
1H
NMR
diamindinitroethylenes
push-pull compounds

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10.1002/mrc.3861

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abstract = "The nitration of tetraiodoethylene (7) yields 1,1-diiodo-2,2- dinitroethylene (8). The latter reacts with alkylamines 9 or alkyldiamines 11 to give the corresponding acyclic 1,1-diamino-2,2-dinitroethylenes 10 or their cyclic analogs 12, respectively. On the basis of liquid and solid-state 13C and 15N NMR data, x-ray analysis and ab initio calculations, we suggest that the title compounds are always zwitterionic and that the CA-CN bond is not a true double bond.",

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AU - Gilinsky-Sharon, Pessia

AU - Gottlieb, Hugo E.

AU - Rajsfus, David E.

AU - Keinan-Adamsky, Keren

AU - Marks, Vered

AU - Aped, Pinchas

AU - Frimer, Aryeh A.

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N2 - The nitration of tetraiodoethylene (7) yields 1,1-diiodo-2,2- dinitroethylene (8). The latter reacts with alkylamines 9 or alkyldiamines 11 to give the corresponding acyclic 1,1-diamino-2,2-dinitroethylenes 10 or their cyclic analogs 12, respectively. On the basis of liquid and solid-state 13C and 15N NMR data, x-ray analysis and ab initio calculations, we suggest that the title compounds are always zwitterionic and that the CA-CN bond is not a true double bond.

AB - The nitration of tetraiodoethylene (7) yields 1,1-diiodo-2,2- dinitroethylene (8). The latter reacts with alkylamines 9 or alkyldiamines 11 to give the corresponding acyclic 1,1-diamino-2,2-dinitroethylenes 10 or their cyclic analogs 12, respectively. On the basis of liquid and solid-state 13C and 15N NMR data, x-ray analysis and ab initio calculations, we suggest that the title compounds are always zwitterionic and that the CA-CN bond is not a true double bond.

KW - 13C

KW - 15N

KW - 1H

KW - NMR

KW - diamindinitroethylenes

KW - push-pull compounds

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JO - Magnetic Resonance in Chemistry

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ER -

1,1-Diamino-2,2-dinitroethylenes are always zwitterions

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Keywords

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