Chemistry rule: elements of period ≥ 3 only form single bonds
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).[1] The double bonds, when they exist, are often weak due to poor orbital overlap between the n>2 orbitals of the two atoms. Although such compounds are not intrinsically unstable, they instead tend to polymerize. An example is the rapid polymerization that occurs upon condensation of disulfur, the heavy analogue of O2. Numerous exceptions to the rule exist.[2]
Double bonds for carbon and nearest neighbours
B boron (n=2)
C carbon (n=2)
N nitrogen (n=2)
O oxygen (n=2)
Si silicon (n=3)
P phosphorus (n=3)
S sulfur (n=3)
B
diborenes
alkylideneboranes
aminoboranylidenes, rare[3]
oxoboranes, rare, rapid oligomerization[4]
borasilenes (rare)[5]
boranylidenephosphanes, rare, stable compounds are known[6]
thioxoboranes, rare[7]
C
alkenes
imines
carbonyls
silenes
phosphaalkenes
thioketones
N
azo compounds
nitroso compounds
silanimines, rare, easy oligomerization, observed only at low temp[8]
phosphazene (P=N)
sulfilimines
O
Singlet oxygen
silanones, Si=O bonds extremely reactive, oligomerization to siloxanes
numerous, e.g. phosphine oxides, phosphonates, phosphinates, phosphates
common compounds such as thiophosphates and phosphine sulfides, for example, triphenylphosphine sulfide and certain dithiadiphosphetanes
S
disulfur, thiosulfoxides
^Jutzi, Peter (1975). "New Element‐Carbon (p‐p)π Bonds". Angewandte Chemie International Edition in English. 14 (4): 232–245. doi:10.1002/anie.197502321.
^West, Robert (2002). "Multiple bonds to silicon: 20 years later". Polyhedron. 21 (5–6): 467–472. doi:10.1016/S0277-5387(01)01017-8.
^ Some research has been done on isomerization of B=NH2 to triple-bonded iminoborane HBNH Rosas-Garcia, Victor M.; Crawford, T. Daniel (2003). "The aminoboranylidene–iminoborane isomerization". The Journal of Chemical Physics. 119 (20): 10647–10652. Bibcode:2003JChPh.11910647R. doi:10.1063/1.1620498.
^Vidovic, Dragoslav; Moore, Jennifer A.; Jones, Jamie N.; Cowley, Alan H. (2005). "Synthesis and Characterization of a Coordinated Oxoborane: Lewis Acid Stabilization of a Boron−Oxygen Double Bond". Journal of the American Chemical Society. 127 (13): 4566–4567. doi:10.1021/ja0507564. PMID 15796509.
^Franz, Daniel; Szilvási, Tibor; Pöthig, Alexander; Inoue, Shigeyoshi (2019). "Isolation of an N‐Heterocyclic Carbene Complex of a Borasilene". Chemistry – A European Journal. 25 (47): 11036–11041. doi:10.1002/chem.201902877. PMID 31241215. S2CID 195660396.
^Example: Ar*P=B(TMP)2, where Ar* is 2,6-dimesityl-phenyl and TMP is 2,2,6,6-tetramethylpiperidine; see Rivard, Eric; Merrill, W. Alexander; Fettinger, James C.; Wolf, Robert; Spikes, Geoffrey H.; Power, Philip P. (2007). "Boron−Pnictogen Multiple Bonds: Donor-Stabilized PB and AsB Bonds and a Hindered Iminoborane with a B−N Triple Bond". Inorganic Chemistry. 46 (8): 2971–2978. doi:10.1021/ic062076n. PMID 17338516.
^Tokitoh, Norihiro; Ito, Mitsuhiro; Okazaki, Renji (1996). "Formation and reactions of a thioxoborane, a novel boron-sulfur double-bond compound". Tetrahedron Letters. 37 (29): 5145–5148. doi:10.1016/0040-4039(96)01039-8.
^Zigler, Steven S.; West, Robert; Michl, Josef (1986). "Observation of a Silanimine in an Inert Matrix and in Solution at Low Temperature". Chemistry Letters. 15 (6): 1025–1028. doi:10.1246/cl.1986.1025.
^Example: Ar*tBuSi=PAr*, where Ar* is 2,4,6-trisiopropylphenyl and tBu is tert-butyl; see Driess, M.; Rell, S.; Merz, K. (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. 625 (7): 1119–1123. doi:10.1002/(SICI)1521-3749(199907)625:7<1119::AID-ZAAC1119>3.0.CO;2-1.
^Suzuki, Hiroyuki; Tokitoh, Norihiro; Nagase, Shigeru; Okazaki, Renji (1994). "The First Genuine Silicon-Sulfur Double-Bond Compound: Synthesis and Crystal Structure of a Kinetically Stabilized Silanethione". Journal of the American Chemical Society. 116 (25): 11578–11579. doi:10.1021/ja00104a052.
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