Abstract
The relative stabilities and reactivities of possible intermediates in the reaction of aniline with formaldehyde under conditions of acid catalysis were estimated by the semiempirical MNDO method. According to the calculation results, protonated N-(hydroxymethyl)aniline and ortho-, meta-, and paraσ-complexes are formed through the ion-dipole complex. Further transformations of these intermediates, which determine the structure of the final products, depend on the possibility of proton abstraction from the σ-complexes with formation of a quinonimine structure, as well as on the lability of the hydroxymethyl group in the protonated amino alcohol.
| Original language | English |
|---|---|
| Pages (from-to) | 679-683 |
| Number of pages | 5 |
| Journal | Russian Journal of Organic Chemistry |
| Volume | 36 |
| Issue number | 5 |
| Publication status | Published - 1 May 2000 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Intermediates in the reaction of aniline with formaldehyde catalyzed by acids. / Bochkarev, V. V.; Soroka, L. S.
In: Russian Journal of Organic Chemistry, Vol. 36, No. 5, 01.05.2000, p. 679-683.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Intermediates in the reaction of aniline with formaldehyde catalyzed by acids
AU - Bochkarev, V. V.
AU - Soroka, L. S.
PY - 2000/5/1
Y1 - 2000/5/1
N2 - The relative stabilities and reactivities of possible intermediates in the reaction of aniline with formaldehyde under conditions of acid catalysis were estimated by the semiempirical MNDO method. According to the calculation results, protonated N-(hydroxymethyl)aniline and ortho-, meta-, and paraσ-complexes are formed through the ion-dipole complex. Further transformations of these intermediates, which determine the structure of the final products, depend on the possibility of proton abstraction from the σ-complexes with formation of a quinonimine structure, as well as on the lability of the hydroxymethyl group in the protonated amino alcohol.
AB - The relative stabilities and reactivities of possible intermediates in the reaction of aniline with formaldehyde under conditions of acid catalysis were estimated by the semiempirical MNDO method. According to the calculation results, protonated N-(hydroxymethyl)aniline and ortho-, meta-, and paraσ-complexes are formed through the ion-dipole complex. Further transformations of these intermediates, which determine the structure of the final products, depend on the possibility of proton abstraction from the σ-complexes with formation of a quinonimine structure, as well as on the lability of the hydroxymethyl group in the protonated amino alcohol.
UR - http://www.scopus.com/inward/record.url?scp=0034178179&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0034178179&partnerID=8YFLogxK
M3 - Article
VL - 36
SP - 679
EP - 683
JO - Russian Journal of Organic Chemistry
JF - Russian Journal of Organic Chemistry
SN - 1070-4280
IS - 5
ER -