1H and 13C NMR assignments of the three dicyclopenta-fused pyrene congeners

María José Otero-Lobato; Cornelis A. van Walree; Remco W.A. Havenith; Leonardus W. Jenneskens; Patrick W. Fowler; Erich Steiner

doi:10.1016/j.tet.2006.03.033

¹H and ¹³C NMR assignments of the three dicyclopenta-fused pyrene congeners

María José Otero-Lobato
, Cornelis A. van Walree
, Remco W.A. Havenith
, Leonardus W. Jenneskens^*
, Patrick W. Fowler
, Erich Steiner

^*Corresponding author voor dit werk

Onderzoeksoutput › Academic › peer review

3 Citaten (Scopus)

Samenvatting

Complete ¹H and ¹³C NMR assignments of the (di-)cyclopenta-fused pyrene congeners, cyclopenta[cd]- (2), dicyclopenta[cd,fg]- (3), dicyclopenta[cd,jk]- (4) and dicyclopenta[cd,mn]pyrene (5), respectively, are achieved using two-dimensional (2D) NMR spectroscopy. The experimental ¹³C chemical shift assignments are compared with computed ab initio CTOCD-PZ2/6-31G^{** 13}C chemical shifts; a satisfactory agreement is found. Substituent-induced chemical shifts in the pyrene core induced by annelation of cyclopenta moieties are discussed. Effects of dicyclopenta topology on electronic structure are illustrated for 3-5.

Originele taal-2	English
Pagina's (van-tot)	5510-5518
Aantal pagina's	9
Tijdschrift	Tetrahedron
Volume	62
Nummer van het tijdschrift	23
DOI's	https://doi.org/10.1016/j.tet.2006.03.033
Status	Published - 5-jun.-2006
Extern gepubliceerd	Ja

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@article{ee82f6387cf94f44baadd892e1b231b4,

title = "1H and 13C NMR assignments of the three dicyclopenta-fused pyrene congeners",

abstract = "Complete 1H and 13C NMR assignments of the (di-)cyclopenta-fused pyrene congeners, cyclopenta[cd]- (2), dicyclopenta[cd,fg]- (3), dicyclopenta[cd,jk]- (4) and dicyclopenta[cd,mn]pyrene (5), respectively, are achieved using two-dimensional (2D) NMR spectroscopy. The experimental 13C chemical shift assignments are compared with computed ab initio CTOCD-PZ2/6-31G** 13C chemical shifts; a satisfactory agreement is found. Substituent-induced chemical shifts in the pyrene core induced by annelation of cyclopenta moieties are discussed. Effects of dicyclopenta topology on electronic structure are illustrated for 3-5.",

author = "Otero-Lobato, \{Mar{\'i}a Jos{\'e}\} and \{van Walree\}, \{Cornelis A.\} and Havenith, \{Remco W.A.\} and Jenneskens, \{Leonardus W.\} and Fowler, \{Patrick W.\} and Erich Steiner",

note = "Funding Information: Financial support from the Basque Country Government (Eusko Jaurlaritza—Gobierno Vasco, Beca para Formaci{\'o}n de Investigadores (M.J.O.-L.)), the Netherlands Organisation for Scientific Research NWO (R.W.A.H., grant 700.53.401) and the Royal Society of Chemistry's Journal Grants for International Authors Programme (0301433, L.W.J.) is gratefully acknowledged.",

year = "2006",

month = jun,

day = "5",

doi = "10.1016/j.tet.2006.03.033",

language = "English",

volume = "62",

pages = "5510--5518",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

number = "23",

}

TY - JOUR

T1 - 1H and 13C NMR assignments of the three dicyclopenta-fused pyrene congeners

AU - Otero-Lobato, María José

AU - van Walree, Cornelis A.

AU - Havenith, Remco W.A.

AU - Jenneskens, Leonardus W.

AU - Fowler, Patrick W.

AU - Steiner, Erich

N1 - Funding Information: Financial support from the Basque Country Government (Eusko Jaurlaritza—Gobierno Vasco, Beca para Formación de Investigadores (M.J.O.-L.)), the Netherlands Organisation for Scientific Research NWO (R.W.A.H., grant 700.53.401) and the Royal Society of Chemistry's Journal Grants for International Authors Programme (0301433, L.W.J.) is gratefully acknowledged.

PY - 2006/6/5

Y1 - 2006/6/5

N2 - Complete 1H and 13C NMR assignments of the (di-)cyclopenta-fused pyrene congeners, cyclopenta[cd]- (2), dicyclopenta[cd,fg]- (3), dicyclopenta[cd,jk]- (4) and dicyclopenta[cd,mn]pyrene (5), respectively, are achieved using two-dimensional (2D) NMR spectroscopy. The experimental 13C chemical shift assignments are compared with computed ab initio CTOCD-PZ2/6-31G** 13C chemical shifts; a satisfactory agreement is found. Substituent-induced chemical shifts in the pyrene core induced by annelation of cyclopenta moieties are discussed. Effects of dicyclopenta topology on electronic structure are illustrated for 3-5.

AB - Complete 1H and 13C NMR assignments of the (di-)cyclopenta-fused pyrene congeners, cyclopenta[cd]- (2), dicyclopenta[cd,fg]- (3), dicyclopenta[cd,jk]- (4) and dicyclopenta[cd,mn]pyrene (5), respectively, are achieved using two-dimensional (2D) NMR spectroscopy. The experimental 13C chemical shift assignments are compared with computed ab initio CTOCD-PZ2/6-31G** 13C chemical shifts; a satisfactory agreement is found. Substituent-induced chemical shifts in the pyrene core induced by annelation of cyclopenta moieties are discussed. Effects of dicyclopenta topology on electronic structure are illustrated for 3-5.

UR - https://www.scopus.com/pages/publications/33646192868

U2 - 10.1016/j.tet.2006.03.033

DO - 10.1016/j.tet.2006.03.033

M3 - Article

AN - SCOPUS:33646192868

SN - 0040-4020

VL - 62

SP - 5510

EP - 5518

JO - Tetrahedron

JF - Tetrahedron

IS - 23

ER -