A C18 Quaternary Ammonium Library

摘要: A library of precursor and functionally active quaternary ammonium cations (QACs) for use as corrosion resistant or antimicrobial coatings, alternatively polymer modifiers, is described. High yielding improved routes to a series terminated allyl ([(CH2=CH-CH2)m-N+(Me)n-C18H37][X−], 1: m=1, n=2, X−=Br−, 3: m=2, n=1, X−=I−, 4: m=3, n=0, X−=Br−) vinyl ([CH2=CHCH2CH2-N+Me2-C18H37][Br−] 5), hydroxy ([HO-(CH2)m-N+Me2-C18H37][Br−], 6: 7: m=4), haloalkyl ([X1-(CH2)3-N+Me2-C18H37][X−] 8: X1=Br, X=Br−, 9: X1=Cl, X=I−), dimethoxyphenethyl ([(MeO)2C6H3(CH2)2-N+Me2-C18H37][Br−], 11), acetamido ([H3C(O)NH-(CH2)3-N+Me2-C18H37][Cl−], 12) cyano ([N≡C–CH2-N+Me2-C18H37][Cl−], 13), organocarbonylamino ([R-C(O)2NH-(CH2)3-N+Me2-C18H37][Br−], 14: R=t-Bu-, 15: R=PhCH2-), phthalimido ([PhthN-(CH2)3-N+Me2-C18H37][Br−], 16), amino ([H2N-(CH2)3-N+Me2-C18H37][Br−] 17), acetylthio ([HC(O)S-(CH2)3-N+Me2-C18H37][Cl−], 18), thiol ([HS-(CH2)3-N+Me2-C18H37][Cl−] 19), disulfa ([-S-(CH2)2-N+Me2-C18H37]2[Br−]2, 20) C18 QACs prepared by thermal microwave driven Menshutkin reactions are detailed. All new compounds were characterized NMR spectroscopy, HRMS spectrometry in the case 1 6 X-ray crystallography.