Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Dinitrogen difluoride: Difference between pages

{{Short description|Chemical compound}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 476992203

| ImageFileL1 = (Z)-Dinitrogen-difluoride.png

| ImageCaptionL1 = ''cis''-dinitrogen difluoride

| ImageFileR1 = (E)-Dinitrogen-difluoride.png

| ImageCaptionR1 = ''trans''-dinitrogen difluoride

| ImageFileL2 = (Z)-Dinitrogen-difluoride-3D-balls.png

| ImageAltL2 = ''cis''-dinitrogen difluoride ball-and-stick model

| ImageFileR2 = (E)-Dinitrogen-difluoride-3D-balls.png

| ImageAltR2 = ''trans''-dinitrogen difluoride ball-and-stick model

{{cite book | last = Lide | first = David R. | year = 1998

| title = Handbook of Chemistry and Physics

| edition = 87th | volume =

| location = Boca Raton, FL

| publisher = CRC Press

| isbn = 0-8493-0594-2 | pages = 4–73, 5–15, 9–46}}</ref>

| IUPACName = ''cis''- or ''trans''-dinitrogen difluoride

| OtherNames = ''cis''- or ''trans''-difluorodiazene

|Section1={{Chembox Identifiers<!-- cis; index=1 -->

| ChemSpiderID1 = 10326121

| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID1_Comment = (''cis'')

| ChemSpiderID2 = 4516471

| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID2_Comment = (''trans'')

| InChI1 = 1S/F2N2/c1-3-4-2/b4-3-

| InChIKey1 = DUQAODNTUBJRGF-ONEGZZNKBY

| InChI1_Comment = (''cis'')

| SMILES1_Comment = (''cis'')

| SMILES2 = F\N=N/F

| SMILES2_Comment = (''trans'')

| InChI3_Ref = {{stdinchicite|correct|chemspider}}

| InChI3 = 1S/F2N2/c1-3-4-2/b4-3+

| InChIKey3_Ref = {{stdinchicite|correct|chemspider}}

| InChIKey3 = DUQAODNTUBJRGF-ARJAWSKDSA-N

| InChI2 = 1/F2N2/c1-3-4-2/b4-3+

| InChIKey2 = DUQAODNTUBJRGF-ONEGZZNKBY

| InChI2_Comment = (''trans'')

| CASNo1_Ref = {{cascite|changed|??}}

| CASNo1 = 13812-43-6

| CASNo1_Comment = (''cis'')

| CASNo2 = 13776-62-0

| CASNo2_Comment = (''trans'')

| PubChem1 = 5364290

| PubChem1_Comment = (''cis'')

| PubChem2 = 5462838

| PubChem2_Comment = (''trans'')

|Section3={{Chembox Properties

| Appearance = Colorless gas

| Formula = FN=NF

| N=2|F=2

| Density = 2.698 g/L

| MeltingPt = ''cis'': less than

| MeltingPtC = −195

| MeltingPt_notes = <br/>''trans'': {{cvt|−172|C|F}}

| BoilingPt = ''cis'':

| BoilingPtC = −105.75

| BoilingPt_notes = <br/>''trans'': {{cvt|−111.45|C|F}}

|Section4={{Chembox Thermochemistry

| DeltaHf = ''cis'': 69.5 kJ/mol<br/>''trans'': 82.0 kJ/mol

| HeatCapacity =

}}

|Section9={{Chembox Related

| OtherAnions = [[Azide]]

| OtherCations = {{ubl|[[Ammonium]]|[[Diazonium compounds]]|[[Pentazenium]]|[[Tetrafluoroammonium]]}}

| OtherFunction_label = Binary fluoro-[[azane]]s

| OtherFunction =

| OtherCompounds = {{ubl|[[Azo compound]]s|[[Diazene]]|[[Triazene]]|[[Tetrazene]]|[[Nitrogen trifluoride]]|[[Tetrafluorohydrazine]]}}

}}

'''Dinitrogen difluoride''' is a [[chemical compound]] with the formula {{chem2|N2F2}}. It is a gas at room temperature, and was first identified in 1952 as the [[thermal decomposition]] product of the [[fluorine azide]] ({{chem2|FN3}}). It has the structure {{chem2|F\sN\dN\sF}} and exists in both [[cis–trans isomerism|''cis'' and ''trans'' isomers]], as typical for [[diimide]]s.

== Isomers ==

The ''cis'' isomer has C_2v symmetry and the ''trans'' isomer has C_2h symmetry. These isomers can interconvert, but the process is slow enough at low temperature that the two can separated by low-temperature [[fractionation]].{{clarify|issue=What type of fractionation (distillation, crystallization, etc.)?|date=January 2024}} The ''trans'' isomer is less [[thermodynamic stability|thermodynamically stable]]<ref>{{Cite journal |last1=Christe |first1=Karl O. |last2=Dixon |first2=David A. |last3=Grant |first3=Daniel J. |last4=Haiges |first4=Ralf |last5=Tham |first5=Fook S. |last6=Vij |first6=Ashwani |last7=Vij |first7=Vandana |last8=Wang |first8=Tsang-Hsiu |last9=Wilson |first9=William W. |date=2010-08-02 |title=Dinitrogen Difluoride Chemistry. Improved Syntheses of cis - and trans -N 2 F 2 , Synthesis and Characterization of N 2 F + Sn 2 F 9 − , Ordered Crystal Structure of N 2 F + Sb 2 F 11 − , High-Level Electronic Structure Calculations of cis -N 2 F 2 , trans -N 2 F 2 , F 2 N═N, and N 2 F + , and Mechanism of the trans−cis Isomerization of N 2 F 2 |url=https://pubs.acs.org/doi/10.1021/ic100471s |journal=Inorganic Chemistry |language=en |volume=49 |issue=15 |pages=6823–6833 |doi=10.1021/ic100471s |pmid=20465274 |issn=0020-1669}}</ref> but can be stored in glass vessels. The ''cis'' isomer attacks glass over a time scale of about 2 weeks to form [[silicon tetrafluoride]] and [[nitrous oxide]]:<ref>{{Greenwood&Earnshaw2nd}}</ref>{{page needed|date=January 2024}}

:{{chem2|2 N2F2 + SiO2 → SiF4 + 2 N2O}}

== Preparation ==

Most preparations of dinitrogen difluoride give mixtures of the two isomers, but they can be prepared independently.

An aqueous method involves ''N'',''N''-difluoro[[urea]] with concentrated [[potassium hydroxide]]. This gives a 40% yield with three times more of the trans isomer.<ref name="Sykes1989">{{cite book|last=Sykes|first=A. G.|title=Advances in Inorganic Chemistry|url=https://books.google.com/books?id=qzN5pnPwuaoC&pg=PA171|accessdate=21 June 2014|date=1989-07-17|publisher=Academic Press|isbn=9780080578828|page=171}}</ref>

[[Difluoramine]] forms a solid unstable compound with [[potassium fluoride]] (or [[rubidium fluoride]] or [[caesium fluoride]]) which decomposes to dinitrogen difluoride.<ref name="Sykes1989"/>

It can also be prepared by [[photolysis]] of [[tetrafluorohydrazine]] and [[bromine]]:<ref name="IS14">{{citation|surname1=Leon M. Zaborowski|display-authors=et al|editor-surname1= Aaron Wold and John K. Ruff|series=Inorganic Syntheses|title=Chlorodifluoroamine and Difluorodiazene - B. Difluorodiazene (Dinitrogen difluoride)|volume=14|publisher=McGraw-Hill Book Company, Inc.|pages=34–39|date=1973|language=German

}}</ref>

:{{chem2|N2F4}} {{overunderset|→|''hv''|{{chem2|Br2}}}} {{chem2|N2F2 + byproducts}}

== Reactions ==

The ''cis'' form of difluorodiazene will react with strong fluoride ion acceptors such as [[antimony pentafluoride]] to form the [[Linear molecular geometry|linear]]<ref name=pubs></ref> {{chem2|[N\tN\sF]+}} cation (fluorodiazonium cation<ref name=pubs>{{cite journal | url=https://pubs.acs.org/doi/10.1021/ic00110a007 | doi=10.1021/ic00110a007 | title=Gaseous Fluorodiazonium Ions. Experimental and Theoretical Study on Formation and Structure of FN2+ | year=1995 | last1=Cacace | first1=Fulvio | last2=Grandinetti | first2=Felice | last3=Pepi | first3=Federico | journal=Inorganic Chemistry | volume=34 | issue=6 | pages=1325–1332 }}</ref>) which forms a [[Salt (chemistry)|salt]] with the formula {{chem2|[N\tN\sF]+[SbF6]−}} (fluorodiazonium hexafluoroantimonate(V)).

:{{chem2|F\sN\dN\sF + SbF5 → [N\tN\sF]+[SbF6]−}}

Analogous reaction of ''cis''-difluorodiazene with [[arsenic pentafluoride]] gives white solid salt with the formula {{chem2|[N\tN\sF]+[AsF6]−}}<ref name=pubs></ref> (fluorodiazonium hexafluoroarsenate(V)).

:{{chem2|F\sN\dN\sF + AsF5 → [N\tN\sF]+[AsF6]−}}

In the solid phase, the observed {{chem2|N\tN}} and {{chem2|N\sF}} bond distances in the {{chem2|[N\tN\sF]+}} cation are 1.089(9) and 1.257(8)&nbsp;Å respectively, among the shortest experimentally observed N-N and N-F bonds.

== References ==

{{reflist}}{{Nitrogen compounds}}

[[Category:Inorganic nitrogen compounds]]

[[Category:Nitrogen fluorides]]

[[Category:Nonmetal halides]]