Skip to main content

Table 1 Summary of selected reactions carried out in this study

From: Prebiotic thiol-catalyzed thioamide bond formation

Reaction

Thioamide produced

Conditions used

Notes

Reducing sulfidic spark

discharge mixture + \(\hbox {CH}_{3}\hbox {SH}\)

Thioformamide

Incubation reaction carried out at RT

See text for spark discharge description

Neutral sulfidic spark

discharge mixture + \(\hbox {CH}_{3}\hbox {SH}\)

Thioformamide

Incubation reaction carried out at RT

See text for spark discharge description

HCN + \(\hbox {H}_{2}\hbox {S}\) + \(\hbox {CH}_{3}\hbox {SH}\)

Thioformamide

pH 7 and 11; 4\(^\circ\)C and RT

Yield of 33% in 48 hours at RT

HCN + \(\hbox {H}_{2}\hbox {S}\)(g) + \(\hbox {CH}_{3}\hbox {SH}\)

Thioformamide

pH 7; RT

–

HCN + \(\hbox {H}_{2}\hbox {S}\) + \(\hbox {CH}_{3}\hbox {CH}_{2}\hbox {SH}\)

Thioformamide

pH 7 and 11; RT

–

HCN + \(\hbox {H}_{2}\hbox {S}\) + cysteamine

None

pH 7; RT

–

HCN + \(\hbox {H}_{2}\hbox {S}\) + N-acetyl cysteamine

None

pH 7; RT

–

HCN + \(\hbox {H}_{2}\hbox {S}\)

None

pH 7 and 11; 4\(^\circ\)C and RT

–

HCN + \(\hbox {H}_{2}\hbox {S}\) + imidazole

None

pH 7; RT

–

3-cyanopyridine + \(\hbox {H}_{2}\hbox {S}\) + \(\hbox {CH}_{3}\hbox {SH}\)

Thionicotinamide

pH 7; 72 hours at RT

Near complete conversion

3-cyanopyridine + \(\hbox {H}_{2}\hbox {S}\)

Thionicotinamide

pH 7; 72 hours at RT

Some product observed, but not as much as with thiol catalyst

  1. Unless stated otherwise, all reactions are carried out in the aqueous phase for 48 h. The identity of the thioamide produced are indicated in the second column. Initial reaction conditions are specified, where RT indicates room temperature