TY - JOUR
T1 - New supramolecular host systems. 41. novel diacetal podands, diazacrowns and cryptands
AU - Frische, Klaus
AU - Greenwald, Moshe
AU - Ashkenasi, Eli
AU - Lemcoff, N. Gabriel
AU - Abramson, Sarah
AU - Golender, Larisa
AU - Fuchs, Benzion
N1 - Funding Information:
for c,6H300,N*. 11: ‘H-NMR (200 MHZ, CDCls) 6 (ppm): 2.81-3.10 (m, 12H, CH2N), 3.48-3.71 (m, 28H, CH20CH2, CH2 (ax), CH). 4.07 (d, ‘J = 12.0 Hz, 2H, CH2 (eq)), 4.81 (m, 2H. OCH); EIMS: m/z (%) = 520 (Mf, 10). [c(]A5 = -6.8 (c=l. chloroform); analysed correctly for C,4H440,0N2. Acknowledgments. This work was supported in part by research grants from the Israel Science Foundation administered by the National Academy of Sciences and from the Ministry of Science and the Arts. A postdoctoral fellowship (to K. F.) from the Kurt Lion Foundation and the Konstanz-Tel-Aviv Forderkreis and a grant-in-aid from the Ministry of Absorption (to L. G.) are gratefully acknowledged. Skillful technical assistance was provided by Mrs. Sarah Weinman.
PY - 1995/12/11
Y1 - 1995/12/11
N2 - New and important key podands bearing the cis-1,3,5,7-tetraoxadecalin (TOD) core are reported, viz., 2,6-di(hydroxymethyl)- (2) and 2,6-di(aminomethyl)-cis-1,3,5,7-TOD (6), which lead to the first diazacrown-TOD compounds (9a) and (9b) and a corresponding cryptand (11) in the series. 9a&b exhibit very good alkali and earth-alkali ion inclusion ability with selectivity for K+ and Ba+2 . Molecular dynamics (Insight/Discover/AMBER) on the crowns and cryptand were performed, including reparametrized MM3-GE calculations. A convincing case for the TOD based hosts was thus established.
AB - New and important key podands bearing the cis-1,3,5,7-tetraoxadecalin (TOD) core are reported, viz., 2,6-di(hydroxymethyl)- (2) and 2,6-di(aminomethyl)-cis-1,3,5,7-TOD (6), which lead to the first diazacrown-TOD compounds (9a) and (9b) and a corresponding cryptand (11) in the series. 9a&b exhibit very good alkali and earth-alkali ion inclusion ability with selectivity for K+ and Ba+2 . Molecular dynamics (Insight/Discover/AMBER) on the crowns and cryptand were performed, including reparametrized MM3-GE calculations. A convincing case for the TOD based hosts was thus established.
UR - http://www.scopus.com/inward/record.url?scp=0028892503&partnerID=8YFLogxK
U2 - 10.1016/0040-4039(95)01938-E
DO - 10.1016/0040-4039(95)01938-E
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AN - SCOPUS:0028892503
SN - 0040-4039
VL - 36
SP - 9193
EP - 9196
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 50
ER -