1,3-dipole

Dipolar compound with electron delocalization and charge separation over 3 atoms 100px120px100px From top to bottom, azides, nitrones, and nitro compounds are examples of 1,3-dipoles. In organic chemistry, a 1,3-dipolar compound or 1,3-dipole is a dipolar compound with delocalized electrons and a separation of charge over three atoms, as follows: the dipole has at least one resonance structure with positive and negative charges having a 1,3 relationship which can generally be denoted as +a\sb\sc-, where a may be a carbon, oxygen or nitrogen, b may be nitrogen or oxygen, and c may be a carbon, oxygen or nitrogen.Jagadamba Singh Photochemistry and Pericyclic Reactions New Academic Science 2009 978-1906574161 100 thumb|402x402px|A demonstration that how some well known 1,3-dipoles like ozone, nitro compounds and azides can be shown to have a resonance structure having 1,3 relationship between positive and negative formal charges They are reactants in 1,3-dipolar cycloadditions.Advanced Organic Chemistry Part A: Structure and mechanisms Francis A. Carey, Richard J. Sundberg 5, illustrated Springer 2007 874 978-0-387-44897-8IUPAC Gold Book dipolar compounds Known 1,3-dipoles are: Azides (RN3) Ozone (O3) Nitro compounds (RNO2) Diazo compounds (R2CN2) Some oxides Azoxide compounds (RN(O)NR) Carbonyl oxides (Criegee zwitterions)https://www.organic-chemistry.org/namedreactions/ozonolysis-criegee-mechanism.shtm Ozonolysis mechanism on Organic Chemistry Portal siteLi, Jie Jack: Criegee mechanism of ozonolysis Book: Name Reactions. 2006, 173-174, 10.1007/3-540-30031-7_77 Nitrile oxides (RCN\sO) Nitrous oxide (N2O) Nitrones (R2CN(R)O) thumb|Carbonyl oxide Some imines: Azomethine imine Nitrilimines (RCN\sNR, analogous to nitrile oxide) Carbonyl imines Some ylides Azomethine ylide Nitrile ylide (RCNCR'2) Carbonyl ylide Thiosulfines (R2CSS) References Category:Organic chemistry