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. 2017 Mar 15;9:19. doi: 10.1186/s13321-017-0205-3

Table 1.

Summary of hydrogen rearrangement rules [9]

Rule ID Ion mode Equationa,b,c Cleaved terminal elementd
P1 Positive M → [M′ − H]+ C, P, S
P2 Positive M → [M′ + H]+ N, O, P, S
P3 Positive M+ → M′+ C, N, O, P, S
P4 Positive M+ → [M′ − 2H]+ C, N, O, P, S
N1 Negative M → [M′ − H] C, N, O, P, S
N2 Negative M → [M′ − 3H] C, P
N3 Negative M → [M′ − 2H] S
N4 Negative M → M′ C, N, O, P, S
N5 Negative M → [M′ − 2H] C, N, O, P, S

aM and M′ indicate the neutralized (hydrogen-supplemented) form

bRules of P1, P2, N1, N2, and N3 consider the neutralized form as the precursor

cRules of P3, P4, N4, and N5 consider the ionized form as the precursor

dBold face indicates the most frequent pattern