Cross-chiral examinations of molecular enantioselective recognition by fast atom bombardment mass spectrometry: Host–guest complexations between chiral crown ethers and chiral organic ammonium ions
✍ Scribed by Masami Sawada; Yasuo Okumura; Hitoshi Yamada; Yoshio Takai; Shigetoshi Takahashi; Takahiro Kaneda; Keiji Hirose; Soichi Misumi
- Publisher
- John Wiley and Sons
- Year
- 1993
- Tongue
- English
- Weight
- 369 KB
- Volume
- 28
- Category
- Article
- ISSN
- 1076-5174
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✦ Synopsis
Using fast atom bombardment (FAB) mass spectrometry (MS), cross-chiral relationships were confirmed for the first time for the diasteromeric host-guest complexations between the chiral crown ether host (1) and the chiral organic ammonium ion guest (2) on the basis of the relative peak intensities (RPI). Both host-guest combinations
(R, R, R, R ) -1, ( R ) -2
and
(S, S, S, S
) -1, (S) -2 obviously provided larger RPI values than the combination of both (R, R, R, R ) -1, (S) -2 and(S, S, S, S) -1, ( R ) -2 by a factor of 1.6 as an averaged value: 1.87 (n = 4)/1.16 (n = 4) = 1.6. These results are consistent with the expected stabilities of the host-guest complexations by CPK model examinations. Successfully observed cross-chiral examinations strongly suggest a potentially useful FABMSPPI methodology for rapidly searching newly designed and synthesized crown ether-like host compounds with a higher degree of enantioselectivity.