Two sources of the decrease of aromaticity:: Bond length alternation and bond elongation.: Part II.: An analysis based on geometry of the singlet and triplet states of 4nπ annulenes:: C4H4, C5H5+, C6H62+, C7H7-, C8H8, C9H9+

被引：42

作者：

Krygowski, TM ^{[1
]}

Cyranski, MK ^{[1
]}

机构：

[1] Univ Warsaw, Dept Chem, PL-02093 Warsaw, Poland

来源：

TETRAHEDRON | 1999年 / 55卷 / 36期

关键词：

aromaticity; annulenes; excited states;

D O I：

10.1016/S0040-4020(99)00629-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Triplet states of 4n pi-electron annulenes exhibit partly aromatic character with an increase of aromaticity as the size of the ring increases. Small effects of dearomatisation are due to bond elongation. Singlet states are antiaromatic. their dearomatisation is mostly due to the bond length alternation. Correlation analysis applied to basic indices of aromaticity (delta(H-1). NICS, HOMA and chi) practically shows the lack of any correlation in sub-groups consisting of triplets or singlets. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：11143 / 11148

页数：6

共 50 条

[1] SYNTHESES AND CRYSTAL-STRUCTURES OF (C8H8)ND(C5H9C5H4)(THF)(2) AND [(C8H8)GD(C5H9C4H4(THF)][(C8H8)GD(C5H9C5H4(THF)(2)]
JIN, JH
ZHUANG, XL
JIN, ZS
CHEN, WQ
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 490 (1-2) : C8 - C13
[2] Role of molecular distortions in the spin-orbit coupling between the singlet and triplet states of the 4π electron systems C4H4, C5H5+, and C3H3-
Shiota, Y
Kondo, M
Yoshizawa, K
JOURNAL OF CHEMICAL PHYSICS, 2001, 115 (20): : 9243 - 9254
[3] An experimental study of the gas-phase bond energies and structures of [c-C4H8S∴c-SC4H8]+, [c-C5H10S∴c-SC4H8]+, and [c-C5H10S∴c-SC5H10]+ and of reactions of [c-C4H8S]+ and [c-C5H10S]+
Illies, AJ
JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (45): : 8774 - 8778
[4] STRUCTURE OF (ETA-5-C9H7)UBR3.C4H8O.OP(C6H5)3
MEUNIERPIRET, J
GERMAIN, G
DECLERCQ, JP
VANMEERSSCHE, M
BULLETIN DES SOCIETES CHIMIQUES BELGES, 1980, 89 (03): : 241 - 245
[5] trans-[(Mo6Cl8)(C7H7)(4){P(n-C4H9)(3)}(2)] and trans-[(Mo6Cl8)(C8H5)(4){P(n-C5H11)(3)}(2)].2C(7)H(8)
Yamagata, T
Okiyama, H
Imoto, H
Saito, T
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1997, 53 : 859 - 862
[6] trans-[(Mo6Cl8)(C7H7)4{P(n-C4H9) 3}2] and trans-[(Mo6Cl8)(C8H5)4{P(n-C5H11) 3}2]&middot-2C7H8
Osaka Univ, Osaka, Japan
Acta Crystallogr Sect C Cryst Struct Commun, pt 7 (859-862):
[7] ISOMERIZATION OF HYDROCARBON IONS .4. ISOMERIC C8H14+. AND C6H10+. IONS AND THEIR C7H11+, C6H9+, C6H7+, AND C6H5+-FRAGMENTS
LEVSEN, K
HILT, E
ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1976, (02): : 257 - 268
[8] Thermochemistry of 4-HOC6H4COR (R = H, CH3, C2H5, n-C3H7, n-C4H9, n-C5H11, and n-C6H13) compounds
Lopes, Catia S. D.
Agapito, Filipe
Bernardes, Carlos E. S.
Minas da Piedade, Manuel E.
JOURNAL OF CHEMICAL THERMODYNAMICS, 2017, 104 : 281 - 287
[9] CARBON K-SHELL EXCITATION OF GASEOUS AND CONDENSED CYCLIC HYDROCARBONS - C3H6, C4H8, C5H8, C5H10, C6H10, C6H12, AND C8H8
HITCHCOCK, AP
NEWBURY, DC
ISHII, I
STOHR, J
HORSLEY, JA
REDWING, RD
JOHNSON, AL
SETTE, F
JOURNAL OF CHEMICAL PHYSICS, 1986, 85 (09): : 4849 - 4862
[10] ENTHALPIES OF FORMATION OF [MO(ETA-C5H5)2(SR)2] COMPLEXES - R=N-C3H7, I-C3H7, N-C4H9, OR T-C4H9
DIAS, AR
SIMOES, JAM
TEIXEIRA, C
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1981, (05): : 1178 - 1179

← 1 2 3 4 5 →