Bond length and reactivity. Structure of 1-methoxymethoxy-3,5-dinitrobenzene, C8H8N2O6

Abstract

Abstract. M r = 228.17, orthorhombic, P212121, a = 5.387 (2), b= 11.053 (2), c= 16.783 (3)A, V= 999.3 (5)/k 3, Z = 4, D x = 1.516 (8) g cm -3, ,~(Mo Ka) = 0.71069 A,/2 = 1-0 cm -1, F(000) = 472, T= 293 K. R =0.041 for 1654 observed reflections. The C-O bond length to the leaving group (referred to acetal hydrolysis) is 1.431 (3)/k; this forms part of a linear correlation between bond length and reactivity in formaldehyde acetals MeOCH2-OR. The conformation about the acetal centre is close to (-sc,-sc) with torsion angles as expected for an acyclic acetal.

Comparison of hydrogen bonds and diverse weak interactions of the nitro group in 2-methyl-4-nitroanilinium nitrate, bisulfate and two hexafluoridosilicates: elementary graph-set approach

“…6d, f and g). The NÁ Á ÁO intermolecular distance is below 3 Å and stays in very good agreement with previously studied crystals (Daszkiewicz, 2013b;Zhang et al, 2000;Jones et al, 1985;Hanson & Hitchcock, 2004;Popova et al, 1987;Klapö tke et al, 2009) and suggests an attraction between the nitro groups (Platts et al, 1995).…”

“…A juxtaposition of the ring patterns showed that they are gradually expanded from the R 2 4 (8) ring. Overall, the nitro group can interact in many modes (Daszkiewicz, 2013b;Zhang et al, 2000;Jones et al, 1985;Hanson & Hitchcock, 2004;Popova et al, 1987;Klapö tke et al, 2009;Trzesowska-Kruszynska, 2015;Roy et al, 2015;Monta- Diversity of weak intermolecular interactions in (a) (H2m4na)NO 3 (1) and (b) (H2m4na)HSO 4 (2). zerozohori et al, 2015;Bauzá & Frontera, 2015;Gagnon et al, 2007;Tsuzuki et al, 2006).…”

Importance of O⋯N interaction between nitro groups in crystals

“…As a result, 104 hits of 57 structures were found. For example, the O4⋯N2 close contact is seen on the normalized Hirshfeld surface 12,13 of 1-methoxymethoxy-3,5-dinitrobenzene 14 (Fig. 1a).…”

Stereoelectronic effects on reactivity. Crystal-structure–reactivity correlations for acetals with synperiplanar lone pairs

“…1a was prepared by the acid-catalysed addition of the alcohol to 3,4-dihydro-2H-pyran. 14 dropwise sodium borohydride (0.185 g, 5 mmol) during 10 min at 0 ЊC. The mixture was stirred for 1 h at room temperature.…”