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Double bond rule

Chemistry rule of thumb

In chemistry, the double bond rule states that elements with a principal quantum number (n) greater than 2 for their valence electrons (period 3 elements and higher) tend not to form multiple bonds (e.g. double bonds and triple bonds). Double bonds for these heavier elements, when they exist, are often weak due to poor orbital overlap between the n2 orbitals of the two atoms. Although such compounds are not intrinsically unstable, they instead tend to dimerize or even polymerize. Moreover, the multiple bonds of the elements with n=2 are much stronger than usual, because lone pair repulsion weakens their sigma bonding but not their pi bonding. An example is the rapid polymerization that occurs upon condensation of disulfur, the heavy analogue of . Numerous exceptions to the rule exist. Several exceptions of this rule have been already made.

		B
boron
(n=2)		C
carbon
(n=2)		N
nitrogen
(n=2)		O
oxygen
(n=2)		width=220	Si
silicon
(n=3)		width=220	P
phosphorus
(n=3)		width=220	S
sulfur
(n=3)	B	C	N	O	Si	P	S
diborenes	alkylideneboranes	doi=10.1063/1.1620498	title=The aminoboranylidene–iminoborane isomerization	year=2003	last1=Rosas-Garcia	first1=Victor M.	last2=Crawford	first2=T. Daniel	journal=The Journal of Chemical Physics	volume=119	issue=20	pages=10647–10652	bibcode=2003JChPh.11910647R}}	doi = 10.1021/ja0507564	title = Synthesis and Characterization of a Coordinated Oxoborane: Lewis Acid Stabilization of a Boron−Oxygen Double Bond	year = 2005	last1 = Vidovic	first1 = Dragoslav	last2 = Moore	first2 = Jennifer A.	last3 = Jones	first3 = Jamie N.	last4 = Cowley	first4 = Alan H.	journal = Journal of the American Chemical Society	volume = 127	issue = 13	pages = 4566–4567	pmid = 15796509	bibcode=2005JAChS.127.4566V }}	title= Isolation of an N-Heterocyclic Carbene Complex of a Borasilene	first1= Daniel	last1= Franz	first2= Tibor	last2= Szilvási	first3= Alexander	last3= Pöthig	first4= Shigeyoshi	last4= Inoue	journal= Chemistry – A European Journal	volume= 25	issue= 47	doi= 10.1002/chem.201902877	year= 2019	pages= 11036–11041	pmid= 31241215	s2cid= 195660396}}	doi=10.1021/ic062076n	title=Boron−Pnictogen Multiple Bonds: Donor-Stabilized PB and AsB Bonds and a Hindered Iminoborane with a B−N Triple Bond	year=2007	last1=Rivard	first1=Eric	last2=Merrill	first2=W. Alexander	last3=Fettinger	first3=James C.	last4=Wolf	first4=Robert	last5=Spikes	first5=Geoffrey H.	last6=Power	first6=Philip P.	journal=Inorganic Chemistry	volume=46	issue=8	pages=2971–2978	pmid=17338516}}	doi=10.1016/0040-4039(96)01039-8	title=Formation and reactions of a thioxoborane, a novel boron–sulfur double-bond compound	year=1996	last1=Tokitoh	first1=Norihiro	last2=Ito	first2=Mitsuhiro	last3=Okazaki	first3=Renji	journal=Tetrahedron Letters	volume=37	issue=29	pages=5145–5148}}
	alkenes	imines	carbonyls	silenes	phosphaalkenes	thioketones
	azo compounds	nitroso compounds	doi = 10.1246/cl.1986.1025	title = Observation of a Silanimine in an Inert Matrix and in Solution at Low Temperature	year = 1986	last1 = Zigler	first1 = Steven S.	last2 = West	first2 = Robert	last3 = Michl	first3 = Josef	journal = Chemistry Letters	volume = 15	issue = 6	pages = 1025–1028}}	phosphazene (P=N)	sulfilimines
	Singlet oxygen	siloxanes]]	numerous, e.g. phosphine oxides, phosphonates, phosphinates,
phosphates	numerous, e.g. sulfuric acid, sulfates, sulfoxides (R-S(=O)-R′, compounds with a sulfinyl group), and sulfones (R-S(=O)2-R′, the sulfonyl group)
	disilenes	tert-butyl]]; see	doi=10.1021/ja00104a052	title=The First Genuine Silicon-Sulfur Double-Bond Compound: Synthesis and Crystal Structure of a Kinetically Stabilized Silanethione	year=1994	last1=Suzuki	first1=Hiroyuki	last2=Tokitoh	first2=Norihiro	last3=Nagase	first3=Shigeru	last4=Okazaki	first4=Renji	journal=Journal of the American Chemical Society	volume=116	issue=25	pages=11578–11579	bibcode=1994JAChS.11611578S }}
	diphosphenes	common compounds such as thiophosphates and phosphine sulfides, for example, triphenylphosphine sulfide and certain dithiadiphosphetanes
	disulfur, thiosulfoxides

Triple bonds

		B
boron
(n=2)		C
carbon
(n=2)		N
nitrogen
(n=2)		O
oxygen
(n=2)		width="220"	Si
silicon
(n=3)		width="220"	P
phosphorus
(n=3)		width="220"	S
sulfur
(n=3)		width=220	Ge
germanium
(n=4)		width=220	As
arsenic
(n=4)	B	C	N	O	Si	P	S	Ge	As
diborynes	Borataalkynes have been observed	Observed in (t-Bu)BN(t-Bu) (an iminoborane)
	alkynes	cyanides	Carbon monoxide (C≡O)	silynes	phosphaalkynes	Carbon monosulfide (C≡S)		arsaalkynes
	Dinitrogen, Diazonium		Phosphorus mononitride (P≡N)		Arsa-diazonium
	Silicon monoxide has some triple-bond character
	disilynes
	Diphosphorus
	Observed in
	Digermyne
	Arsenic monophosphide (As≡P)

References

(1975). "New Element-Carbon (p-p)π Bonds". Angewandte Chemie International Edition in English.
(1984). "Chemical Bonding in Higher Main Group Elements". Angewandte Chemie International Edition.
(2002). "Multiple bonds to silicon: 20 years later". Polyhedron.
Power, Philip P.. (2020-12-14). "An Update on Multiple Bonding between Heavier Main Group Elements: The Importance of Pauli Repulsion, Charge-Shift Character, and London Dispersion Force Effects". Organometallics.
(2003). "The aminoboranylidene–iminoborane isomerization". The Journal of Chemical Physics.
(2005). "Synthesis and Characterization of a Coordinated Oxoborane: Lewis Acid Stabilization of a Boron−Oxygen Double Bond". Journal of the American Chemical Society.
(2019). "Isolation of an ''N''-Heterocyclic Carbene Complex of a Borasilene". Chemistry – A European Journal.
(2007). "Boron−Pnictogen Multiple Bonds: Donor-Stabilized PB and AsB Bonds and a Hindered Iminoborane with a B−N Triple Bond". Inorganic Chemistry.
(1996). "Formation and reactions of a thioxoborane, a novel boron–sulfur double-bond compound". Tetrahedron Letters.
(1986). "Observation of a Silanimine in an Inert Matrix and in Solution at Low Temperature". Chemistry Letters.
(1999). "Ungewöhnliche Reaktivität der Silicium-Phosphor-Doppelbindung in einem Silyliden(fluorsilyl)phosphan: Intramolekulare C,H-Inserierung und seine Umwandlung in ein neues Silyliden(silyl)phosphan". Zeitschrift für Anorganische und Allgemeine Chemie.
(1994). "The First Genuine Silicon-Sulfur Double-Bond Compound: Synthesis and Crystal Structure of a Kinetically Stabilized Silanethione". Journal of the American Chemical Society.
(1990). "Compounds with a Boron–Carbon Triple Bond". Angew. Chem. Int. Ed. Engl..
(2013). "Arsa-Diazonium Salts With an Arsenic–Nitrogen Triple Bond". Angew. Chem. Int. Ed. Engl..
Ritter, Stephen K.. (March 21, 2005). "Sulfur's Turn for Multiple Bonds". Chemical & Engineering News.

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