Bridge Flipping Data from Dynamic 1H‐NMR Spectra of 2,6‐Dimethyl‐[9](3,5)‐Pyridophane and its Pyrylium and N‐Methylpyridinium Analogs

Alexandru T. Balaban, Teodor‐Silviu ‐S Balaban, Makoto Nitta, Nobuhiro Kanomata

    Research output: Contribution to journalArticle

    3 Citations (Scopus)

    Abstract

    Dynamic 1H‐NMR spectra between room temperature and −90 °C for the title compounds indicate that the flipping of the nonamethylene bridge is slowed down on cooling (ΔGc‡ = 9.8 kcal/mol for the 2/8 methylene groups in the pyridinophane with coalescence temperature Tc = −58 °C) but the pseudorotation persists even at −90 °C. The bridge flipping is somewhat easier in the N‐methylpyridinium (ΔGc‡ = 9.7 kcal/mol, Tc = −63 °C) and in the pyrylophanium perchlorates (ΔGc‡ = 8.9 kcal/mol, Tc = −78 °C).

    Original languageEnglish
    Pages (from-to)1047-1051
    Number of pages5
    JournalBulletin des Sociétés Chimiques Belges
    Volume101
    Issue number12
    DOIs
    Publication statusPublished - 1992

    Fingerprint

    Perchlorates
    Coalescence
    Cooling
    Temperature

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Bridge Flipping Data from Dynamic 1H‐NMR Spectra of 2,6‐Dimethyl‐[9](3,5)‐Pyridophane and its Pyrylium and N‐Methylpyridinium Analogs. / Balaban, Alexandru T.; Balaban, Teodor‐Silviu ‐S; Nitta, Makoto; Kanomata, Nobuhiro.

    In: Bulletin des Sociétés Chimiques Belges, Vol. 101, No. 12, 1992, p. 1047-1051.

    Research output: Contribution to journalArticle

    @article{d780f18bd77b420fbcba6729211600c3,
    title = "Bridge Flipping Data from Dynamic 1H‐NMR Spectra of 2,6‐Dimethyl‐[9](3,5)‐Pyridophane and its Pyrylium and N‐Methylpyridinium Analogs",
    abstract = "Dynamic 1H‐NMR spectra between room temperature and −90 °C for the title compounds indicate that the flipping of the nonamethylene bridge is slowed down on cooling (ΔGc‡ = 9.8 kcal/mol for the 2/8 methylene groups in the pyridinophane with coalescence temperature Tc = −58 °C) but the pseudorotation persists even at −90 °C. The bridge flipping is somewhat easier in the N‐methylpyridinium (ΔGc‡ = 9.7 kcal/mol, Tc = −63 °C) and in the pyrylophanium perchlorates (ΔGc‡ = 8.9 kcal/mol, Tc = −78 °C).",
    author = "Balaban, {Alexandru T.} and Balaban, {Teodor‐Silviu ‐S} and Makoto Nitta and Nobuhiro Kanomata",
    year = "1992",
    doi = "10.1002/bscb.19921011210",
    language = "English",
    volume = "101",
    pages = "1047--1051",
    journal = "Bulletin des Societes Chimiques Belges",
    issn = "0037-9646",
    publisher = "John Wiley and Sons Ltd",
    number = "12",

    }

    TY - JOUR

    T1 - Bridge Flipping Data from Dynamic 1H‐NMR Spectra of 2,6‐Dimethyl‐[9](3,5)‐Pyridophane and its Pyrylium and N‐Methylpyridinium Analogs

    AU - Balaban, Alexandru T.

    AU - Balaban, Teodor‐Silviu ‐S

    AU - Nitta, Makoto

    AU - Kanomata, Nobuhiro

    PY - 1992

    Y1 - 1992

    N2 - Dynamic 1H‐NMR spectra between room temperature and −90 °C for the title compounds indicate that the flipping of the nonamethylene bridge is slowed down on cooling (ΔGc‡ = 9.8 kcal/mol for the 2/8 methylene groups in the pyridinophane with coalescence temperature Tc = −58 °C) but the pseudorotation persists even at −90 °C. The bridge flipping is somewhat easier in the N‐methylpyridinium (ΔGc‡ = 9.7 kcal/mol, Tc = −63 °C) and in the pyrylophanium perchlorates (ΔGc‡ = 8.9 kcal/mol, Tc = −78 °C).

    AB - Dynamic 1H‐NMR spectra between room temperature and −90 °C for the title compounds indicate that the flipping of the nonamethylene bridge is slowed down on cooling (ΔGc‡ = 9.8 kcal/mol for the 2/8 methylene groups in the pyridinophane with coalescence temperature Tc = −58 °C) but the pseudorotation persists even at −90 °C. The bridge flipping is somewhat easier in the N‐methylpyridinium (ΔGc‡ = 9.7 kcal/mol, Tc = −63 °C) and in the pyrylophanium perchlorates (ΔGc‡ = 8.9 kcal/mol, Tc = −78 °C).

    UR - http://www.scopus.com/inward/record.url?scp=0343876500&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=0343876500&partnerID=8YFLogxK

    U2 - 10.1002/bscb.19921011210

    DO - 10.1002/bscb.19921011210

    M3 - Article

    AN - SCOPUS:0343876500

    VL - 101

    SP - 1047

    EP - 1051

    JO - Bulletin des Societes Chimiques Belges

    JF - Bulletin des Societes Chimiques Belges

    SN - 0037-9646

    IS - 12

    ER -