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. 2019 Jun 11;116(26):12660–12665. doi: 10.1073/pnas.1816039116

Table 2.

Top 10 substrates over the history of chemistry

Top	Before 1860	1860–1879	1880–1889	1900–1919	1920–1939	1940–1959	1960–1979	1980–1999	2000–2015
1	$H_{2}$ O	$H_{2}$ O	HCl	EtOH	EtOH	${A c}_{2}$ O	${A c}_{2}$ O	${A c}_{2}$ O	${A c}_{2}$ O
2	${N H}_{3}$	HCl	EtOH	HCl	AcOH	EtOH	MeOH	MeOH	MeOH
3	${H N O}_{3}$	EtOH	$H_{2}$ O	AcOH	HCl	AcOH	${C H}_{2} N_{2}$	MeI	$H_{2}$ O
4	HCl	$H_{2} {S O}_{4}$	AcOH	$H_{2}$ O	${A c}_{2}$ O	$H_{2}$ O	MeI	${C H}_{2} N_{2}$	MeI
5	$H_{2} {S O}_{4}$	${H N O}_{3}$	${A c}_{2}$ O	${A c}_{2}$ O	$H_{2}$ O	MeOH	${C H}_{2}$ O	${C H}_{2}$ O	PhCHO
6	EtOH	${B r}_{2}$	$H_{2} {S O}_{4}$	$H_{2} {S O}_{4}$	${E t}_{2}$ O	HCl	EtOH	PhCHO	${C H}_{2}$ O
7	${C l}_{2}$	AcOH	MeI	MeI	$H_{2} {S O}_{4}$	$C_{6} H_{6}$	Morph	CuO	CO
8	${N a}_{2} {C O}_{3}$	${N H}_{3}$	${P h N H}_{2}$	${E t}_{2}$ O	$C_{6} H_{6}$	${E t}_{2}$ O	${P h N H}_{2}$	EtOH	TFA
9	KOH	${P h N H}_{2}$	${H N O}_{3}$	${P h N H}_{2}$	MeOH	${C H}_{2}$ O	DMA	BzCl	PhAcet
10	$I_{2}$	MeI	${B r}_{2}$	MeOH	${B r}_{2}$	MeI	PhCHO	CO	BnBr

Abbreviations are defined in Materials and Methods.