%AWidner, Danielle [Department of Chemistry University of Wisconsin‐Stevens Point 2001 Fourth Avenue WI 54481 Stevens Point US]%AWidner, Danielle [Department of Chemistry; University of Wisconsin-Stevens Point; 2001 Fourth Avenue WI 54481 Stevens Point US]%ARobinson, Emily [Department of Chemistry University of Wisconsin‐Stevens Point 2001 Fourth Avenue WI 54481 Stevens Point US]%ARobinson, Emily [Department of Chemistry; University of Wisconsin-Stevens Point; 2001 Fourth Avenue WI 54481 Stevens Point US]%APerez, Alejandra [Department of Chemistry University of Wisconsin‐Stevens Point 2001 Fourth Avenue WI 54481 Stevens Point US]%APerez, Alejandra [Department of Chemistry; University of Wisconsin-Stevens Point; 2001 Fourth Avenue WI 54481 Stevens Point US]%AVang, Herh [Department of Chemistry University of Wisconsin‐Stevens Point 2001 Fourth Avenue WI 54481 Stevens Point US]%AVang, Herh [Department of Chemistry; University of Wisconsin-Stevens Point; 2001 Fourth Avenue WI 54481 Stevens Point US]%AThorson, Rachel [Department of Chemistry University of Wisconsin‐Stevens Point 2001 Fourth Avenue WI 54481 Stevens Point US]%AThorson, Rachel [Department of Chemistry; University of Wisconsin-Stevens Point; 2001 Fourth Avenue WI 54481 Stevens Point US]%ADriscoll, Zakarias [Department of Chemistry; University of Wisconsin-Stevens Point; 2001 Fourth Avenue WI 54481 Stevens Point US]%ADriscoll, Zakarias [Department of Chemistry University of Wisconsin‐Stevens Point 2001 Fourth Avenue WI 54481 Stevens Point US]%AGiebel, Sierra [Department of Chemistry; University of Wisconsin-Stevens Point; 2001 Fourth Avenue WI 54481 Stevens Point US]%AGiebel, Sierra [Department of Chemistry University of Wisconsin‐Stevens Point 2001 Fourth Avenue WI 54481 Stevens Point US]%ABerndt, Calvin [Department of Chemistry University of Wisconsin‐Stevens Point 2001 Fourth Avenue WI 54481 Stevens Point US]%ABerndt, Calvin [Department of Chemistry; University of Wisconsin-Stevens Point; 2001 Fourth Avenue WI 54481 Stevens Point US]%ABosch, Eric [Department of Chemistry Missouri State University 901 S. National Ave. MO 65897 Springfield US]%ABosch, Eric [Department of Chemistry; Missouri State University; 901 S. National Ave. MO 65897 Springfield US]%ASpeetzen, Erin [Department of Chemistry University of Wisconsin‐Stevens Point 2001 Fourth Avenue WI 54481 Stevens Point US]%ASpeetzen, Erin [Department of Chemistry; University of Wisconsin-Stevens Point; 2001 Fourth Avenue WI 54481 Stevens Point US]%ABowling, Nathan [Department of Chemistry University of Wisconsin‐Stevens Point 2001 Fourth Avenue WI 54481 Stevens Point US]%ABowling, Nathan [Department of Chemistry; University of Wisconsin-Stevens Point; 2001 Fourth Avenue WI 54481 Stevens Point US]%BJournal Name: European Journal of Organic Chemistry; Journal Volume: 2017; Journal Issue: 38; Related Information: CHORUS Timestamp: 2023-10-06 03:46:18 %D2017%IWiley Blackwell (John Wiley & Sons) %JJournal Name: European Journal of Organic Chemistry; Journal Volume: 2017; Journal Issue: 38; Related Information: CHORUS Timestamp: 2023-10-06 03:46:18 %K %MOSTI ID: 10044658 %PMedium: X; Size: p. 5739-5749 %TComparing Strong and Weak Halogen Bonding in Solution: 13 C NMR, UV/Vis, Crystallographic, and Computational Studies of an Intramolecular Model %X

A series of arylene ethynylene compounds has been generated in order to study the differences between strong and weak intramolecular halogen bonding in solution. With strong intramolecular halogen bonding, the presence of electron‐withdrawing fluorine substituents near the halogen‐bond donor has a significant impact on the halogen bond and consequently on13C NMR chemical shifts. UV/Vis studies suggest increased conjugation of the arylene ethynylene backbone when strong halogen bonds are present. UV/Vis and NMR signatures of intramolecular halogen bonding are diminished significantly when electron‐withdrawing fluorine substituents are absent, however. This change in behavior is further illustrated by differences in crystallization tendencies with the presence or absence of electron‐withdrawing substituents. Calculations using the M06‐2X functional provide some insight into the energies associated with both strong and weak intramolecular halogen bonding.

%0Journal Article