Molecular structures and reactivities of 1,3-diphthalimidobenzene derivatives

A. Yu Kovalevsky; O. V. Shishkin; I. I. Ponomarev

doi:10.1007/BF02503483

Molecular structures and reactivities of 1,3-diphthalimidobenzene derivatives

A. Yu Kovalevsky
, O. V. Shishkin
, I. I. Ponomarev

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

Abstract

X-ray diffraction analysis of 4,6-di(morpholin-4-yl) and 4,6-di(2,2,2-trifluoroethoxy) derivatives of 1,3-diphthalimidobenzene, which are potent reagents in the synthesis of heterocyclic polymers, was carried out. The conjugation between the π-systems of the benzene ring and of the phthalimide and morpholine substituents is distorted due to the rotation of the substituents about the C(Ar)-N bonds. The AMI calculations demonstrated that the hydrogen atoms of the methylene groups are "acidic," which is favorable for condensation reactions. Steric hindrances to intramolecular condensation were estimated.

Original language	English
Pages (from-to)	1122-1129
Number of pages	8
Journal	Russian Chemical Bulletin
Volume	47
Issue number	6
DOIs	https://doi.org/10.1007/BF02503483
State	Published - Jun 1998
Externally published	Yes

Funding

This work was partially supported by the Russian Foundation for Basic Research (Project No. 97-03-33783) and by the Program "Leading Scientific Schools" (Project No. 96-15-97367).

Keywords

1,3-diphthalimidobenzene
AMI method
Charge distribution
Molecular structure

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10.1007/BF02503483

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title = "Molecular structures and reactivities of 1,3-diphthalimidobenzene derivatives",

abstract = "X-ray diffraction analysis of 4,6-di(morpholin-4-yl) and 4,6-di(2,2,2-trifluoroethoxy) derivatives of 1,3-diphthalimidobenzene, which are potent reagents in the synthesis of heterocyclic polymers, was carried out. The conjugation between the π-systems of the benzene ring and of the phthalimide and morpholine substituents is distorted due to the rotation of the substituents about the C(Ar)-N bonds. The AMI calculations demonstrated that the hydrogen atoms of the methylene groups are {"}acidic,{"} which is favorable for condensation reactions. Steric hindrances to intramolecular condensation were estimated.",

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year = "1998",

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doi = "10.1007/BF02503483",

language = "English",

volume = "47",

pages = "1122--1129",

journal = "Russian Chemical Bulletin",

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T1 - Molecular structures and reactivities of 1,3-diphthalimidobenzene derivatives

AU - Kovalevsky, A. Yu

AU - Shishkin, O. V.

AU - Ponomarev, I. I.

PY - 1998/6

Y1 - 1998/6

N2 - X-ray diffraction analysis of 4,6-di(morpholin-4-yl) and 4,6-di(2,2,2-trifluoroethoxy) derivatives of 1,3-diphthalimidobenzene, which are potent reagents in the synthesis of heterocyclic polymers, was carried out. The conjugation between the π-systems of the benzene ring and of the phthalimide and morpholine substituents is distorted due to the rotation of the substituents about the C(Ar)-N bonds. The AMI calculations demonstrated that the hydrogen atoms of the methylene groups are "acidic," which is favorable for condensation reactions. Steric hindrances to intramolecular condensation were estimated.

AB - X-ray diffraction analysis of 4,6-di(morpholin-4-yl) and 4,6-di(2,2,2-trifluoroethoxy) derivatives of 1,3-diphthalimidobenzene, which are potent reagents in the synthesis of heterocyclic polymers, was carried out. The conjugation between the π-systems of the benzene ring and of the phthalimide and morpholine substituents is distorted due to the rotation of the substituents about the C(Ar)-N bonds. The AMI calculations demonstrated that the hydrogen atoms of the methylene groups are "acidic," which is favorable for condensation reactions. Steric hindrances to intramolecular condensation were estimated.

KW - 1,3-diphthalimidobenzene

KW - AMI method

KW - Charge distribution

KW - Molecular structure

UR - https://www.scopus.com/pages/publications/0032399321

U2 - 10.1007/BF02503483

DO - 10.1007/BF02503483

M3 - Article

AN - SCOPUS:0032399321

SN - 1066-5285

VL - 47

SP - 1122

EP - 1129

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

IS - 6

ER -

Molecular structures and reactivities of 1,3-diphthalimidobenzene derivatives

Abstract

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