Hydrogen-deuterium exchange reactions of cis- and trans-cyclopropane derivatives with D2O and CD3OD in the gas phase

✍ Scribed by Zhili Li; Shuying Liu

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 136 KB
• Volume: 14
• Category: Article
• ISSN: 0951-4198
• DOI: 10.1002/(sici)1097-0231(20000215)14:3<180::aid-rcm855>3.0.co;2-k

✦ Synopsis

Gas-phase hydrogen-deuterium (H/D) exchange reactions involving four isomeric cyclopropane derivatives were investigated under chemical ionization (CI) conditions, using D(2)O and CD(3)OD as reagent gases. There are abundant ions at M + 1, M + 2 and M + 3 in the D(2)O and CD(3)OD positive-ion CI mass spectra of the two isomer pairs 1, 2 and 3, 4. Their CI mass spectra are identical with each pair, and so are the collision-induced dissociation (CID) spectra of ions M + 1, M + 2 and M + 3 of each of the two isomer pairs. The CID spectra of M + 1 ions indicate that they have common D/H exchange reactions within each pair, which take place between molecular ions and deuterium-labeling reagents to form the M - H + D ions. Those of their M + 2 ions show that they have common D/H exchange reactions within each pair, which form the M(d1) + H ions. Those of their M + 3 ions show that they have common D/H exchange reactions within each pair, which take place between the [M(d1)] and deuterium-labeling reagents to produce M(d2) + H for the isomer pair 1, 2 and M(d1) + D for the isomer pair 3, 4. The number and position, and active order of the active hydrogen atoms of the isomer pairs 1, 2 and 3, 4 were determined. Copyright 2000 John Wiley & Sons, Ltd.