N-Hydroxysuccinimide

Abstract

Key indicatorsSingle-crystal X-ray study T = 133 K Mean '(C±C) = 0.002 A Ê R factor = 0.041 wR factor = 0.108 Data-to-parameter ratio = 11.2 For details of how these key indicators were automatically derived from the article, see

2,5-Dioxopyrrolidin-1-yl methanesulfonate

“…1) is displaced from the plane of adjacent C1, C4 and O1 atoms by 0.220 (2) Å , in good agreement with the data for known sulfonic derivatives of Noxyimides, that is, in the range 0.150 (1)-0.243 (2) Å (Grigorieva & Chetkina, 1977;Stefanowicz et al, 2005Stefanowicz et al, , 2006. This geometric feature in (I) was not observed for the almost planar N-hydroxyimides (Karolak-Wojciechowska et al, 1993;Miao et al, 1995;Abell & Oldham, 1999;Jones, 2003) or slightly puckered N-halogensuccinimides (Brown, 1961). The N1-O1 bond length (Table 1) is slightly longer than the distances observed for N-hydroxysuccinimide (Jones, 2003), for the other N-hydroxyimides (Karolak-Wojciechowska et al, 1993;Miao et al, 1995) and for 1-[(2-naphthylsulfonyl)oxy]pyrrolidine-2,5-dione (Stefanowicz et al, 2005).…”

“…The N1-O1 bond length (Table 1) is slightly longer than the distances observed for N-hydroxysuccinimide (Jones, 2003), for the other N-hydroxyimides (Karolak-Wojciechowska et al, 1993;Miao et al, 1995) and for 1-[(2-naphthylsulfonyl)oxy]pyrrolidine-2,5-dione (Stefanowicz et al, 2005). The C1-N1 and N1-C4 bond lengths are slightly longer than typical C-N values for N-hydroxysuccinimide and its derivatives [1.365 (2)-1.392 (2) Å ; Karolak-Wojciechowska et al, 1993;Miao et al, 1995;Abell & Oldham, 1999;Jones, 2003]. These values also correspond with C-N bond lengths observed for the sulfonic esters of N-hydroxyimides (Stefanowicz et al, 2005(Stefanowicz et al, , 2006.…”

“…This geometric feature in (I) was not observed for the almost planar N-hydroxyimides (Karolak-Wojciechowska et al, 1993;Miao et al, 1995;Abell & Oldham, 1999;Jones, 2003) or slightly puckered N-halogensuccinimides (Brown, 1961). The N1-O1 bond length (Table 1) is slightly longer than the distances observed for N-hydroxysuccinimide (Jones, 2003), for the other N-hydroxyimides (Karolak-Wojciechowska et al, 1993;Miao et al, 1995) and for 1-[(2-naphthylsulfonyl)oxy]pyrrolidine-2,5-dione (Stefanowicz et al, 2005). The C1-N1 and N1-C4 bond lengths are slightly longer than typical C-N values for N-hydroxysuccinimide and its derivatives [1.365 (2)-1.392 (2) Å ; Karolak-Wojciechowska et al, 1993;Miao et al, 1995;Abell & Oldham, 1999;Jones, 2003].…”

2,5-Dioxopyrrolidin-1-yl 3-(furan-2-yl)acrylate

“…For derivatives of N-hydroxysuccinimide, see: Anderson et al (1964); Blumberg & Vallee (1975); Brown et al (2005); Cheng et al (2007); Jones (2003 Table 1 Hydrogen-bond geometry (Å , ). Symmetry codes: (i) x À 1 2 ; y; Àz þ 1 2 ; (ii) x À 1 2 ; y À 1; Àz þ 1 2 .…”

“…Comment N-Hydroxysuccinimide is frequently used in organic chemistry as an activating reagent, which readily form crystalline adducts with amines or acids (Jones, 2003). N-Hydroxysuccinimide esters are widely used as leaving groups to activate carboxylic acids (Cheng et al, 2007).…”